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Windward System Five

Cloud-based business management solution | ERP for your SMB

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Windward System Five Pricing

Pricing overview

Value for money rating

3.8

/5

171

Price starts from

129

/user

Per month

Pricing options
Free plan
Subscription
Free trial

Pricing details

Pricing plans range from $99 to $129* per user per month, plus a one-time implementation fee.
*based on user count.
Note: Windward Software typically bills yearly, monthly rates are for comparative purposes. Talk to your rep for options.

What users say

Once live, it just got worse and worse. In hindsight, I should have listened to my gut in implementation, written the money invested off as a bad business decision and aborted.

ZW

Zoe W.

Amazing inventory control and accounting is up to date without costing a fortune in labour or software.

LC

Leslie C.

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Reviewers who mentioned pricing said:

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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A powerful POS with unlimited flexibility, reliable stability, and great support staff.

Reviewed 5 years ago

Saved our company time and money in the ling run. Being able to customize the look, feel, and functions of the application let us implement EXACTLY what our company needed. We evaluated MANY other products before choosing Windward, and nothing comes close. It was one of the better decisions made in our organization, and is a big personal red-feather in my hat.

Pros

- Extremely customizable. Allows you to customize anything from report, to custom price-labels, to customized POS screen (even changing the size/color/look of virtually every button). If you are a little more adventurous, you can even write code that allows you make your own functions. - Easy to learn. For as advanced as this is, most people can pick up on the majority what thy need in a day. ...

Cons

- Price tag will be your biggest hurdle. And some features will cost you extra. Having to pay extra to have the software integrate with our merchant account is probably the biggest complaint I have with the company. But even this is vastly outweighed by the Pros. If you want the best, it probably isn't going to be the cheapest. - There are occasional errors that pop up and random issues. But 90% of these are self-resolving (very intuitive software). For the other 10%, support is right there to remote in and stay with you until it's resolve.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend3/10

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System Five

Reviewed 10 days ago

Service and online capability was not good. While we paid for 24/7 service, we had to setup tickets and would get a call back within 24hrs.

Pros

The built in reports allowed for easily customizing reports. With their "lookup words" it was easy to tag, customers, products and vendors to particular categories for additional reporting

Cons

The online capability. There was no good capability for online. Sales would take a long time to integrate back into the software and there was no direct connection between Windward S5 to the online platform such as WooCommerce. Which meant an additional cost for another API connection. Windward API was very limited to what info could be pushed and pulled from the website.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend7/10

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windward system 5

Reviewed 11 days ago

Overall system 5 is an end to end solution which we count on to mange our business. We would like to see regular scheduled maintaince as part of our annual subscription plan. We have invested heavily in to the software on the years and would.lien to feel we can get value added serviced included.

Pros

The software is an end to end solution for our business - we like this alot. This last year the software has slowed down which has created inefficiencies.

Cons

The software performance has dropped as we add more users and increase the date base. The length of time it takes to book appointments has been increasing over the last two years

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend6/10

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Learning Curves

Reviewed 10 days ago

About 2.5 months in, and a good portion was correcting issues that we didn't have time to fix before going live. Still refining but it keeps getting better as we go. At first I was intimidated by how exact you have to be when some of the wording is ambiguous, but once you learn what the system means/wants, its a breeze and has saved us tens of hours already. I think with a more comprehensive set-up program this system would be easier to use.

Pros

The software seems able to do nearly anything necessary, except for a few odds and ends like creating a report for a single salesperson for a set date period for each supplier, for SPIFF purposes. Plenty of automated systems, the required orders feature is nice.

Cons

The amount of tabs, and vernacular used, often make it more difficult to do a simple operation. Integrating with XO Logic has been a chore, and still isn't completed yet. Pricing/cost import issues, that are fine on our website managed by XO, but not reflecting/importing correctly across vendors into our System 5 POS.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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Windward and You. The tutorial.

Reviewed a year ago

We have solved issues with double ordering Special Orders, have streamlined Purchase Orders, Receiving, Price Changes, Showroom tag printing. I am able to compile reports simply, where it use to take days. Taking inventory is so much faster using data collectors and being able to import the files.

Pros

Our old system was very outdated and Windward has made it so much simpler and quicker to get our monthly/quarterly reports. Integration between order taking and purchasing has helped speed up the ordering process & stop mistakes being made. Love the virtual warehouse option.

Cons

What i feel is missing is: 1. Freeform 1 & 2 can be data loaded in. Freeform 1 can be on a report, but Freeform 2 can not. 2. Sales/Upsell warnings can be on a report, but not data loaded. 3. Purchase warnings can be data loaded, but not put on a report. (Invoice Warnings can be data loaded & put on a report) 4. There is no where to search "Non-Stock Special Orders" by number or supplier in history. 5....

Vendor response

Hi Todd, Thanks for taking the time to write this! Other lighting showrooms that may be considering Windward will find this helpful. As for your reporting concerns, we may be able to help through a project plan from the professional services catalog which would be a great place to start to explore existing functionality. https://www.windwardsoftware.com/resources/professional-services.html There is also the option to do some custom programming if you have requirements that cannot be handled by the current reporting tools. We are looking forward to many more years of service to Grand Rapids Lighting. Thanks again Todd!

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support

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Gets the job done. Do not do the updates.

Reviewed 5 years ago
Pros

Very thorough software with lots of room/areas to store Information and very easy to use. The point and click ability of the software makes it easier to train new staff. Can access the software from anywhere in the world using remote desktop connection.

Cons

The updates do not seem to go very smoothly. And update me fix one problem but two new problems arise that were not problems before. We have actually stopped getting updates and have continued to use our current version for years. We have developed our own internal ways to use the software to its fullest potential without getting updates. Software support is readily available however very expensive...

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend9/10

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I depend on Windward every day for my role in sales and marketing. I couldn't do my job without it!

Reviewed 5 years ago

It's integral to my role in the company. In fact everyone in our company uses Windward on a daily basis. We use it in every aspect of our product based business from order processing, to sales, management, warranty, accounting and inventory management.

Pros

I like the ability to generate custom sales reports so I can see who my top dealer accounts are, and which accounts I need to incentivize. I need to quickly check stock of products in all four of our warehouse locations, and when a product is out of stock, I need to be able to quickly see what's been ordered and when we are expecting it to arrive at our warehouses. In a "just in time delivery" business...

Cons

Like any feature packed program, intuitive menus are critical to accessing all the nuances of the software. Most of power software programs leave something to be desired in the area of intuitive interfaces. Windward is no exception to this. Thus, task specific training modules and quick customer support is of utmost importance to users being able to shorten the learning curve when expanding their knowledge of Windward.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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Highly customizable software that you can really tailor to your business for an affordable price.

Reviewed 5 years ago

Reduced IT costs, Improved staff experience and greater overall efficiency of our business practices.

Pros

I give this review after having tried many different software packages over the last 15 years. Some costing x10 the price of Windard, some costing x10 less. What I'm left with over these years is perspective, and that perspective was hard earned. You will not find a more complete point of sale, inventory control, accounting, crm, etc. for this price range. With the ability to fine tune...

Cons

There is no such thing as perfect software. With that being said, there are issues...but then it's technology. You have to considering that it is a highly customizable product that able to serve an amazing range of business types with thousands of options. What Windward has that sets it apart is a fantastic support team with Canadian staff and an out-of-country team that is admittingly fantastic...probably...

Vendor response

Mark, thank you very much for taking the time to provide your feedback on your experience with Windward System Five. We're thrilled that you are very satisfied with our software! As you identify in your review, Windward Software is committed to continuously improving our business management solutions such that we may continue to offer the most user-friendly, yet comprehensive functionality available.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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Windward- Success for Power Equipment, Construction Supplies and Rental

Reviewed 5 years ago

We have been using System 5 since 2003. The system has scaled to our operation as we grow. The accounting side is robust and handles all our AP- AR- and General Ledger needs. Purchasing is fully automated. Billing customers can be fully modified with "Types" and "subTypes" to keep the status of orders updated and classified. Our inventory and product locations have been controlled and managed with...

Pros

We could not run our business without the information and order that the system provides! 1. Ease of use- Everything is in one program 2. Total integration- We don't need to transfer data to another program like QuickBooks 3. Strong Accounting, Control, and reports- Ability to customize GL and P&L format and multiple years. 4. Hundreds of pre-built Reports- We rarely do custom 5. Ability to create...

Cons

Probably not really a con But there are so many features available, it take some time to learn and put them into daily practice. The rest are just enhancements we'd like to see !! First, We would like to see the RMA system simplified. Second, we would like to see the E-commerce platform developed more. We are using it now for our website, but we would like to see more features and search options. Third, we would like to see the Timecard function developed and enhanced. Fourth, we would like to see the offering of more credit card processing options. Fifth, we would like the ability to attach PDF's to items, instead of JPG. But all in all, the system works really well!

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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Scalable multi-user POS retail from a company that listens and adapts.

Reviewed 7 years ago
Pros

Excellent customer support 24/7. A product that is scalable to your business. One of the few softwares that have a stand-a-lone ability that allow sales and lookup when the main server is offline or unavailable. Inventory orders in cases or singles by multiple suppliers with multiple part numbers and UPC codes for a single item. Capable of printing price tags on the fly when receiving. Easy lookup...

Cons

Back office reporting is probably the weekest area. However, custom reports are available and creatable. If you are looking into any software you should have a list of what you need to know daily, weekly and monthly and have it demonstrated to you. Another area is handling price protection from manufacturers. It is not easy to drop cost on items that receive price protection. It can be done but is time consuming.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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This softwear has made our business extremely essential to operate.

Reviewed 5 years ago

the main function of our business, our retail set up revolves around the software making it easy to operate day to week, to month to yearly. it has been absolutely essential. recording & keeping track of everything form our substantial amount of inventory, along with accounting, reports, staff, ect. our main source of operations for sure. :)

Pros

that is is absolutely fluent in keeping all of our information organized & keeps me able to do my job as a 1 woman Owner/Operator. without this softwear we would not have been able to stay open for the past 11 years without the ease of Windward System 5, for my retail business.

Cons

for us a small retail shop, the maintenance & updating costs are quite high & out of our price range on a year to year basis.

Vendor response

Hi Marie, thank you for taking the time to provide feedback relating to your experience with Windward System Five. We're very happy to see that it's significantly helping the operation of your business! With regard to maintenance & updating, please contact your Account Manager at +1 (800) 663-5750, at your convenience, to discuss options to determine the most cost-effective solution. For example, it may be optimal to transfer to Windward System Five on Cloud, which includes automatic data backups and installation of updates and does not require your business to use a server.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support

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13 years with System 5

Reviewed 6 years ago

I installed System 5 for my "brick and mortar" business in 2003. This is one of the best investments I have made for my business. I have thousands of parts & customers, and hundreds of suppliers. Most of my inventory is tracked by serial number. "Windward" is pretty quick in spite of my huge database, and the interface makes it very easy to look up info (such as customer past purchase history,...

Pros

No pros were added to this review

Cons

No cons were added to this review

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support

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An Amazing Experience with Windward System Five

Reviewed 7 years ago

Since we have moved onto Windward System Five the improvement to our business have been and still remain extraordinary. System Five has given me the ability to work in an environment with real time information. With complete integration my business can process sales, my office team can work on accounting and financial transactions, inventory can be taken, purchase orders can be processed and more,...

Pros

No pros were added to this review

Cons

No cons were added to this review

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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Best system around if you are willing to put the effort in before you go live, super easy POS side.

Reviewed 5 years ago

Best system I have ever used, to date have implemented this system in 2 businesses. This system has increased speed of transactions and lowered overheads. Best all round system.

Pros

Have put this system in 2 businesses have had no real issues to date that have not been easy to fix. POS is pretty flawless and easy to use. You can report on just about anything. Support staff are fantastic, and implementation was easy. Windward are with you the whole way making sure everything works.

Cons

To date have non, anything that I have ever had an issue with usually stems from user error. There are some processes that I would like to have, and they can absolutely be custom programed, like seeing what items on the invoice are have customer contract pricing, but this does not affect most sales and can be checked other ways. So not really a con just something that my end would be great, more than likely there is a way to do this. I am always learning new things to stream line the process.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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Customizable to a variety of business types. Fairly easy to use and learn the basics.

Reviewed 5 years ago

One software that we can use for the front end of the business and the back.

Pros

I like being able to customize buttons at the cash registers and change them seasonally as we are a garden center and our products do change drastically with the seasons. Customer support is always very helpful and has fixed most issues that I have had in the past. We make our nursery signs, labels, and a variety of different types of price tags within System Five. No need for another program as we did need one in the past. I have not used them yet but having webinars and a learning area available to us is an excellent way to get more out of our software.

Cons

Customer tech support is very good, however I think that it is a bit expensive annually. The label and form designers work but do not seem to be what you see is what you get. It takes a little finessing to create a label that fits your media properly.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend3/10

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Good for the price. We've been a user since the DOS days.

Reviewed 5 years ago

Far cheaper than our old system. Also much better feature set.

Pros

Many features - most of them even work. Price is pretty good compared to most solutions. It generally works and if you don't do any updates you get used to the bugs and how to work around them.

Cons

Bugs. Every update fixes some bugs and introduces some new ones. I don't bother with updates anymore, just too many headaches. Slightly archaic - you can feel that it is not a fully modern product. Years (decades) of upgrades and patches have made it feel like no one person can manage the whole project anymore. Fixes in one area screws things up in another. Service is spotty. Pervasive SQL is utter garbage and you don't have a choice to run another SQL server. Pervasive is easily the worst part of this whole system. We've added ecommerce to our business but haven't integrated System 5 - the cost is eye-watering. Maybe if the cost comes down at some point.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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SOFTWARD THAT DOES IT ALL

Reviewed 5 years ago

It took a little time to learn the features but we have been very pleased with how this software works for us in our retail Hobby Shop. We have a huge inventory which is constantly changing - no problem for Windward. Windward handles our point of sale including receivables. Tracks our purchases and payables and allows us to create reports and bar codes and so much more. I can't imagine a type of business that could not function with this very extensive software at a reasonable price. Lots of good updates and fast help available when you need it.

Pros

Ability to design inventory reports that provide us detail on what has been sold in a date range and allows us to purchase wisely.

Cons

Only one thing I would like to see added: A report to show income and expense in a spreadsheet by month.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support

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I wish I never heard of Windward Software

Reviewed 2 years ago

Our overall experience was extremely poor and detrimental to our business. All our staff were frustrated ( I nearly lost staff), some customers were frustrated, we invested so much money, and have in turn lost so much money. Oh and did I mention the time invested. All that time I spent, all a waste, the time my staff spent which I paid for, such a waste. So much stress that my whole team went through...

Pros

We are a retail shop with a mechanic workshop out the back. The special order process was a positive, but unfortunately when you think of all the difficulties, costs and time loss from the rest of the system I can't go so far as to say it is a pro. The idea of the detailed security and reports options is good, but due to extensive glitches never realized any benefits. Unfortunately the reports and...

Cons

The implementation is long and tedious. We worked hard with 'technicians' to ensure quality data was loaded. We had 5 different implementation technicians as 2 left the company, one they allocated to us didn't suit the timezone, one provided intermittent help, & one was finally helpful. Windward waived some licencing fees to compensate for lack of support as we were paying for a licence we could not...

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend5/10

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Basic programming and intigration issues.

Reviewed 4 days ago

Having trouble intigrating Windward System Five, with shipping programs.

Pros

Easy for the sales people to use, once they are very familiar with the system.

Cons

There are basic programming errors, such as date changes, Currency type, etc. that do not flow through the je, you have to change existing je's line by line. The control numbers should change what is in the je. When I addressed the issue, I was brushed off and just told to adjust the entries. When you try to use a date range for printing vendor accounts it does not work. Trying to get it to work with other programs has been a problem, and everthing has a price tag associated with it.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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Wondward Software is taking us to the next level of POS sales, service & support.

Reviewed 5 years ago

An All in One Sales, Customer tracking, Promo & follow up, Bookkeeping & Accounting Software With Great Support.

Pros

Back office accounting is saving us money by tracking inventory vs sales, as well as less cost with accounting fees by running an all inclusive bookkeeping/accounting program.

Cons

The occasional glitches, after each windows update, with form display screens freezing up the software.

Vendor response

Thank you, Ed, for taking the time to provide us with your feedback and for your positive comments: much appreciated! We are committed to ensuring that Windward System Five is 100% seamless in operation with all future Windows releases. That said, if you experience any issues please contact our Customer Support Team at any time for assistance: +1 (800) 663-5750.

Overall Rating
  • Value for money
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  • Customer support

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Best Value

Reviewed 8 years ago

Although the implementation of this solution is a lot of work, I have been through others in the past and this one was not much different. You do have to pay extra if you want them to come on site and help, otherwise you are left to watch videos and meet on the phone/over the PC with them. They did help build out a custom learning curriculum for us and help facilitate the learning for my staff which...

Pros

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Cons

No cons were added to this review

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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Overall this software has a lot of capabilities that integrate easily into our company.

Reviewed 5 years ago

It saves me time. We used to run and inventory program, a bookkeeping program and an ecommerce program. It combined these 3 programs into one.

Pros

That it is easy to train our employees on. Great help videos! I really like their integrated ecommerce. It is nice to update one price in our system and to have that price automatically updated on our website.

Cons

Not so great for my outside sales staff. We run their WEAR program for our outside staff. It tends to have errors as it is similar to running just a backup version. I also wish that their ecommerce did not run in HTML only

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend9/10

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Its a very powerful software and has huge potential.

Reviewed 5 years ago

It forced us to realize how many things we were doing wrong and we will be a much stronger company then our competition when we finally get it all setup. We are still learning everyday better techniques.

Pros

Tons of custom options that our previous software hadn't even thought of. Love the custom print outs Barcodes take a bit to figure out but then the potential is huge. Custom settings as simple as a specific printer for a specific printout. Can limit employee access super specifically Inventory system is really flexible and powerful

Cons

Would be nice to be able to do price file updates during the day. You have to have everyone logged out to do it. This partially for data integrity. The WEAR software still needs some work can't see the virtual warehouse and has some minor kinks that need to be worked out in the latest version.

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend1/10

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I have a 8 user licence. Many bugs and some functionality falls short. As if they did not think the whole process through properly. Financial side is very cumbersome. I am looking for alternate solutions.

Reviewed 5 years ago

Read all the reviews. This software could really be good if it was finished strong and some further thought was applied to the processes. It seems 80% complete with shortfalls in many areas. Financials are just not suitable for our size of business. It takes 4x the amount of time to complete a task compared to QB. My accountants find this aspect frustrating. They really should offer an integration with QB for those who want it. It feels like they are trying to cover too much in this software. I have some tickets on issues and bugs for over 3 months now and they still have not been completed. Of what I know now, I would not have purchased this software. I am looking for alternate software.

Pros

The sales aspect is good. POS is acceptable. Easy to find a product and sell it. Kits work well. Reporting is somewhat good. Support tries to resolve issues.

Cons

Financials - If you are serious about your business, this is not for you. It is not comparable to Quick books. They have flatly refused to integrate with QB. Their financial side scores a 1/10. The Multi currency module is full of promise but has many problems and bugs like display and operational issues. You have to be very careful when dealing with multi-currency. Procurement is quite basic and could...

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend9/10

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**Windward Software

Reviewed 6 years ago

Windward has been a great company to work with. We had some trouble during the start up of the system, and because of that we are still working out some kinks but Windward's support team has been great to deal with and are always available. The sales team has been easy to work with. For us, the system was the one of the only ones out there which had the full integration of all the services that we needed or anticipated needing in the future, and at a relatively good price point.

Pros

Full integration

Cons

Scheduling doesn't match up as closely with the way we would like to use it as possible.