There are lots and lots of resources for help. Almost every page on the Moodle site has a link at the bottom of it taking you to the specific documentation of what you are working with. Moodle has a huge community of worldwide users that are extremely responsive to user forums, so help is literally a couple of clicks away.
Moodle is easy to figure out, even if you have never used and LMS. The site I currently administrate is at http://classes.ala.org. As you land on the homepage, you will see the list of our different divisions who offer online courses. We do this using the categories feature, allowing each of our separate divisions to be represented on the single ALA site. What you might also notice is that the login for the site is a convenient eyebrow link. If you click it, there are a variety of options for setting up your own guest credentials in addition to signing in with your official credentials granted by one of the administrators.
Most user issues are simple to troubleshoot. Moodle's no nonsense layout and intuitive interaction makes it pretty straightforward to figure out user issues. Error messages tell you specifically what a problem is in plain English (or whatever language you want to set up). Most user problems are rights related in the system.
Moodle allows you to restore previous courses into new courses. The backup and restore feature pretty much does everything for you. Take out the user data from a backup and you can restore the previous version of a course into a brand new course with very little downtime.
Version 1.9 requires an older version of Java running in order to use the wysiwyg html editor (something that comes in handy for the introduction to the course and each section/Topic for the course) -- a version of Java is required, that if you are on Windows 7, has security issues that your Network Admin is probably blocking.
The workaround not having an html editor is to open your web content editor (we have Drupal and Dreamweaver) and then paste the code into the setting fields. It is not difficult to do, just inconvenient. I am sure the current version 2.6 has this capability and more that we are waiting to upgrade to.
You have to dig a bit to get to the settings and permissions for specific activities. For example, a common user issue is with Student access to a forum. It is not obvious that some forums are specifically for teacher announcements (meaning that students aren't able to respond, just read the announcements). By the time I get issue, the course creator has a dozen or so forums setup with participants already subscribed, which means that it is easier for me to go into each forum and override the native rights. When you have scores of courses running each containing a dozen or more forums that each need to have permissions touched, it is a lot of work from the admin point of view. The lighter side is that with the proper training, or sandbox playing, creators can discover this nuance before its' too late.
The native chat activity doesn't really work in version 1.9. We use FlashChat by Host123 when our course leaders need a course chat room.
In version 1.9, there is not a lot of wiggle room in changing the look and feel of the courses. You can add, subtract and move blocks around, you can assign a theme, but it is not the most modern look and feel.