For simplicity, buy a used ipad. Android tablets are a b**** to maintain if you're not into customizing it. And because they're older and sometimes obselete, the support dries up into one or two custom roms which may or may not be fully stable. That said, android tablets have a much better value for initial price. Depends on your time and interest.
Buy him a used Nintendo DS or PS Vita. A used portable game console can be easily found for less than $100.
Best tablet for seniors to Skÿpe with people? Needs to be simple and of course, have a ruggedized case available.
Thanks, everyone. Ended up getting a couple of these: http://www.amazon.com/gp/product/B00S26CQO2?psc=1&redirect=true&ref_=oh_aui_detailpage_o00_s00 Paid with my Discover card and used points (that I wasn't even aware I had) and ended up getting both for free!