a) Probably, but since we can't "see inside your head" we really can't answer that question. There are training resources, books and tutorials tha can help you get a broad based introduction to FileMaker--even some tutorials on YouTube and we'll be glad to answer any specific questions that you have here in this forum.
b) If you design the layouts/scripts/value lists to be easy to use, the average user should have no trouble using the database. You'll probably find that you have many more layout design options in FileMaker than Bento. The end user should not require any special skills beyond the ability to read. (Of course the more familiar they are with other programs, the less effort will be needed to show them how your layouts work, but a properly designed layout should be fairly self explanatory...)
Thanks, that's good to know.
I should have asked as an overall question whether you would recommend using Filemaker instead of Bento for this task?
Also, I have seen the resources on filemaker.com and have seen some videos available on youtube (lynda.com ones), but if you or anyone else has any links to free resources that are good, that would be amazing
Not being a Mac user, I have never used Bento. My impression from posts made by others is that Filemaker will be the better option, but "your mileage will vary" as the added options for how you can design the system that FileMaker provides also means that it will result in a steeper "learning curve" for you.