DynastyStar: Recently, I got Fantasy General on GOG because I bought other games on the GOG Winter Sale, but it looks so dated but I can't feel like I'm being a bit judgemental. I had the same problem awhile back when GOG gave me a free copy of both Fallout 1 and 2, time doesn't seem to have been good to those games. However, I feel like chances are if I played some older games that hook me well that I'll be able to get used to older games.
Does anybody have any suggestions? What works best for me is forcing myself not to check my phone or alt-tab, older games demand more attention. After two to five hours, I'm engulfed by the mechanics and/or story and I forget that it's an older game I'm playing. That is if the game is any good, not every game ages well.
Games that doesn't age well needs nostalgia to work at all, but sometimes even that isn't enough. Some good memories should remain just that, good memories.
Planescape: Torment is an excellent suggestion if you enjoy reading books. The characters in that game felt more alive to me than the characters in The Witcher 3, the vivid language/text in that game is fantastic. The way the isometric pixly characters feel full of life and personality is truly remarakble.
Knights of the Old Republic is also great. It's right between modern and old, and the perfect gateway if you enjoy Star Wars. If you get used the Knights of the Old Republic due to mildly simplified mechanics, you might as well enjoy older rpgs from the golden era since they are pretty similar.