My questions are:
1. Is it reasonable to think we can get this laptop up and running just to allow him limited access to the internet?
2. Will I have to purchase any updated hardware/software?
3. How do I figure out if the sites he visits are compatible with this older software?
I know this is a tl;dr but again, I'm a technological idot so I really don't know much about what I'm talking about (as usual). I can try to answer any questions to the best of my ability if it leads to help figuring this out....
The easiest way to find out is to do a fresh install of windows, get rid of any software you won't be using, download firefox and net nanny or some equivalent and see if the sites work. My guess is you might be light on RAM, but ram for older machines can get expensive so I'd just give it a shot with what you have