Also, any ex-con-in-tech related advice is welcome.
Is he allowed books (defining your scope of 'printed')? They'd be so much better than printing a web site.
Becoming a Google Apps consultant might be a good route and get him going quickly. Knowing how to take a company's workflow into Docs, Sheets, etc., is as much methodology as it is tech and code. If he's got good people skills, can see flow at a higher level, this requires very little to get started. The docs are pretty decent but I don't know how many pages this will take to print https://developers.google.com/apps-script/overview
For something more technical, perhaps take a look at the django project's docs. https://www.djangoproject.com/start/
It's going to take some work to get things set up and there's a lot of stuff that's going to be scary new.
But with minimal tweaking it offers a really decent admin interface that's relatively easy to customize and apply input rules, just like an Access database.
Python is relatively easy for BASIC programmers to pick up and loops, decision logic, that kind of thing is directly translatable with very little learning.
I got started professionally with dBase back in the dark ages, jumping from amateur BASIC on a Commodore PET. If he's inquisitive, hungry, determined, and willing to put in the hours there's a journey to getting current again.
Good luck to your dad and I hope you get some useful advice from this thread.