Yeah that’s true. I made a Visual Basic game on DirectDraw like 20 years ago and it still runs great
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I use Linux, and Proton/WINE is good for emulating a lot of them 
It is also part of the appeal for me honestly, I enjoy making stuff work.
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I also enjoy doing this - esp when starting a new franchise I want to play the original release first and then the games in release order to see how they influence sequels and change over time.
With franchises it’s practically absolutely necessary to me; I find seeing the way that those develop to be the most interesting part of playing any given game in a franchise. Glad to see someone else does the same!
I get my curiosity peaked when I’m talking with friends and they come up, for instance we started chatting about Blitz The League during the Super Bowl and 5 mins later I’m downloading it
Someone metions an old game that looks interesting, I make a mental note to one day play it
At any point between later the same day and 10 years later, I’ll remember that mental note and go play it
A more active way is also picking a system, looking up lists of games for that system getting what looks interesting
Also another point for browsing My Abandoware. That site rules
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I struggle with this. Decision paralysis and ADHD has been complicated further by having just about everything available at our fingertips. Since becoming A Journal Guy, I’ve started keeping a log of things I want to play. I think it helps, though I’ve found I’m very good at making lists rather than playing things. Your mileage may vary.
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Honestly, for me it’s been simple: I either play things I never managed to finish originally OR games I wish I could have played but either couldn’t because of hardare limitations or simply didn’t get around to. Of course, I also replay things I’ve enjoyed and tend to get very different things out of them as an adult 
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Decision paralysis can hit me hard. So sometimes I’ll use polls, or in discord servers that disable it, I can set up letter emoticons to let others react to. I think it works out well.
Other times, I try something for a bit, and see if it lands with me.
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I think the most consistent way that I’ve played and finished retro games is with a group focusing on a console library and talking about them together. Like, a bunch of people saying, hey, let’s play some Saturn games. Maybe people pick the same ones and maybe not, but it at least sets a field of play and discourse.
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