This kind of thinking needs to die. Non-tech people are the ones who benefit MOST from the nice ecosystem and user experience of Apple. They are the ones who NEED these kinds of devices to make it work for them. You might be able to deal with the crappiness and issues that come up with a cheap device, but he can't. If you want him to be successful in any way with new technology, pay the money for the product that is most positioned to do that.
I think the iPhone 7 is probably a good one to get. Still not too old and there's very little difference with the 8, except for the glass back that can easily break on the 8. You can still set the view mode, bold fonts, etc... on the 7.