I’ve run into these issues in the few years since I’ve switched. Old outdated stuff or windows exclusive software can be a hassle to get running. Possible, but your putting a square peg in a round hole.
Were flatpaks a thing when you tried Linux last? Flatpak makes installing most programs extremely easy. I just search my distros software store and hit install. As a bonus, you often get newer versions than when you install software traditionally, and updates can be set to automatically download.
I’ve run Pop OS since 2019. I have never reinstalled and I only touch the terminal maybe once every 6 months. Absolutely everything I do is GUI.
I have a small dumb TV I got fairly recently from Best Buy. It’s their store brand and has no smart features. Only 720p but they had some 1080p ones too. They’re nothing special but very cheap. Mine was an open box and I got it for maybe 40 or 50 dollars.