There's an archived thread about replaying old games here:
https://www.gog.com/forum/general_archive/replaying_titles

I've recently started to not only replay those games 10+ years later, but making notes on how I install and run them on a modern Linux. Even the games that were released with Linux binaries don't fare well with the current state of the OS, As well, WINE, PlayOnLinux, and Crossover have progressed enough that these older games play well and are enjoyable, especially when updated with hi-res texture packs.

I've tried to document for myself what I had to do and what files and mods I used here:
http://www.maximumhoyt.com

I just recently became aware of the https://www.gog.com/forum/general/the_judas_does_this_run_in_wine_thread_v1173 thread and have great appreciation for someone who can slog their way through so many games and solve so many problems.

I have been working through all the Quakes, the Unreals and many of the Wolfensteins, all of which I purchased retail years ago or from GOG. I'm delighted to see such community support for these games.

A few of these games I never finished, so there are still new things for me to discover.

What are you replaying now?

almost done with a Fallout replay

had been in the middle of a Rebel Assault replay but got discouraged when I couldn't beat one of the Hoth missions after like 30 tries - joystick with the game just isn't as reactive as things were back in the day, it's annoying

I'm replaying Deus Ex, only my second playthrough after 17 years. Back then, I was running on a system below minimum requirements, I have no idea how I ever completed the game. And back then it was intimidating since I gave the AI much more credit than they were due. Years of subsequent 3D and stealth gaming experience have taught me how to 'game' the AI by keeping just the right distance, using cover, and moving just slowly enough so that they don't notice me. I'm going for a stealthy mostly non-lethal playthrough, since in my first run I played run-and-gun like most other shooters of the day, and I want to make different plot choices this time, like saving Paul.

Just replayed Dust: An Elysian Tail. I didn't bother to 4-star the trials, and I didn't bother with Tough (which doesn't really have anything to offer that Hardcore doesn't) or Casual (which is actually quite fun, since you have infinite dust storm and fidget power) difficulties.

I am planning on giving Morrowind another go. It should be interesting coming back after having played Oblivion (before, I had only played Arena and Daggerfall).

I just finished replaying The Secret of Monkey Island, which is possibly my most replayed game, but it had been a long while since my previous playthrough. It was as fun as the first day!

There were a few things, mostly small details, that I didn't remember, so it was amazing to still find something new. There was particularly a scene (where you speak with a random NPC) that struck me as totally unseen before. I don't know if I just had never been there before (you need to stray away from the obvious path), it's been so long that I didn't remember it, or if it was added in the Special Edition.

I will definitely keep replaying classic games.

Replaying Max Payne 2. To this day I think second chapter is the best in the series. Smooth gameplay, slo-mo mechanics better updated, the game itself has the same atmosphere or sometimes even greater than 1.

Also, replaying Brothers in Arms: Road to hill 30. This game brings so good memories back in a day when it was released. For me best WW2 game series. If you like tv series Band of Brothers or Steven's Spielberg gem Saving Private Ryan you must play this series. Still waiting 4 installment to this day. I hope Gearbox Software will soon release it