When it comes to D&D, I'd rather shave my eyebrows off with a cheese grater than go back and play any edition with THAC0. And I'm saying that as someone who has very, very fond memories of AD&D 1st and 2nd edition. But I'm not the same gamer that I was thirty years ago. If I see a newer version of a game that's been around for 30+ years, I'm probably going to go with that under the assumption that it's changed a little bit to be more palatable to a modern audience. An assumption that might get me in trouble with a game like Call of Cthulhu.
But then your point out another good reason why I'd generally go with the more recent edition. It isn't just that it's the new hotness, but because it's going to be more widely available than the older version. At least that's how it used to be, right now if you want Cyberpunk 2020 books you can find them on Drive Thru RPG in the form of PDF or books. I'm fortunate in that my regular group is generally willing to try different types of games, but the D&D effect is real, and it can be hard to find people interested in other games. If I want to play a game of Shadowrun it's probably easier to find someone for 6th edition than it is for 1st edition.