He's not into computers at all and is a "use it until it crumbles to dust before you buy a new one" kind of person. He has about six analog TVs in his house. He doesn't want to pay for cable, and I had to explain the concept of converter boxes to him so he could use a cheap digital antenna to watch over the air channels (he was running out of garage sales to obtain VHS VCRs that he had hooked up to everything to watch the 200-something VHS tapes he'd recorded of TV shows since the 1980s, and the tapes were starting to erode and break VCRs they were played in as well. Some of them have mold on them from the basement and he still wants to keep them and record shows on them because he has so many tapes he refuses to throw away...) Once he got the idea, he wanted to put a digital antenna and converter on every TV he has. I said "If you're going to that expense, why don't you buy one or two inexpensive flatscreen TVs (they can be had for ~$150 in the sizes he needs) and you don't have to buy all the converter boxes?" He pooh-poohed that idea because he already has enough TVs.
I finally handed down to him the first 36" flatscreen HD TV I had ever purchased about 15 (?) years ago when I replaced it with a 55" UHD and I didn't have a place for a fourth extra screen. (My new TV cost $200 less than I paid for the 36" back in the day, and despite being HUGE, is flatter and weighs 20 pounds less. Ah, technology!) He had to ask me three times where the other speaker wires were.
I finally got a call from him saying he understands what he was missing now - the picture is clearer and stronger (since the TV is already digital he's not going through another component) and he didn't realize broadcast signals are now in HD for free. Now he's working on how to start replacing all his old SD 200-pound tube sets (some of them missing colors) with new flat screens. My only comment was "Welcome to the 21st Century, Pop!"
Now if I can convince him to get internet in his house so he can do all the research and online shopping I do for him. Once he had to coordinate with people arranging a get-together by email with me as the point of contact and that was a farce of epic proportions.