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 Old outdated stuff or windows exclusive software can be a hassle to get running.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.