Your dad sounds a lot like my mom. Even down the the Ramblers in the 60's. No color TV, only a 17" B&W on a roll-around stand.I'm trying not to complicate things, we got him a 65" Sony 4K 900 series 2 years ago when we moved him from Las Vegas to Oklahoma City. The Plex app is on his TV, right next to YouTube, which he watches incessantly. He gets confused about which remote to use, so I set it up so he can use the Sony remote for everything, including Cox Cable. (I hid the Cox remotes in his nightstand)
I wanted to get him the 65" Sony because it had a great picture and he was moving his 40" Sony to the bedroom and replacing the 32" Sony there. He wanted to get a TCL 55" series 4, so when we got to Best Buy I proceeded with my plan. I showed him how much better the picture was on the Sony, how the software interface was so familiar, how much better the sound was. Unfortunately he kept comparing the prices, Sony $1700/TCL $600.
I think in my past life, I must have sold used cars, because, first I reminded him that in his lifetime he had NEVER gone near the "Top Shelf" items. Heck he went thru a 10 year period from 1960 to 1970 when he drove Ramblers, although the '64 Rambler Ambassador he bought new was really nice, he could have gotten a Chevelle SS or a GTO. In '63 I lobbied for a Jag XKE, but that's a whole nother story.
Anyway, it turned out that Best Buy was sold out of the TCLs, that was when I went in with my "Rock Bottom" deal. I told him if he paid the $600 for the TCL, I'd pay the $1100 difference to get him the Sony. He stepped back and asked why I would do that?
So, I took a deep breath, stepped up, put my hand on his 90 year old shoulder, and told the truth.
"Dad, I would really rather inherit the Sony."
Probably the Great Depression made a big impact on both. She would have been 103 this year.