I have worked with sycamore as a parent, staff member, and super user (software administrator) over the last 7 years. What makes Sycamore work so well, is that it is constantly growing and making enhancements as the needs of it's users grow yet still keeping to the same "feel" and design so that students, parents and teachers don't have to re-learn the software every time there is an enhancement.
The software itself is pretty comprehensive and has been easy to use. We have several schools in our district using the software as well, so as parents move from Elementary School to Middle to our High School, they have appreciated not having to learn a new platform, and those that come from outside our district have commented on how easy it was to make the transition. New teachers grasp on to it's layout very quickly.
It's hard to really talk about cons, because anytime I have found a quirk or issue, Sycamore has been very receptive to those concerns and actively found a solution or came up with an enhancement. They are always growing the product. Which leads me to their support system and customer service. Most of the time I can find my answers in their Online manual or videos. When I need a bit more help, as a Sycamore Super User, can submit a support ticket any time of day and will get a response within the hour...very very rarely have I not connected with a live person when I have phoned, which I rarely have to do. The support staff is well educated in the software and the nicest people you will ever talk/chat with. As a teacher, you can chat anytime during the school day with a support tech, even just to ask a "where do I find" question...no question is too menial.
Overall, you will never find an SIS that meets every schools needs or ways of doing things, so what becomes important is finding an SIS that does the job, is continually growing and advancing, and provides outstanding customer service. This is what Sycamore provides it's customers.
Ease of use