My two are Morrowind, where I loved the quest design and lack of handholding, but the random hit chance and BS difficulty distribution were just... too much to handle.

And also, KOTOR, which I expected to love as a huge Star Wars fan, but the "stand around while dice are rolled" combat was just... exceptionally boring and tedious.

I feel like after BotW and TotK, older 3D Zelda games seem clunky yet easy. I can't get used to the cameras in OoT and MM it feels so stiff as opposed to an old game like Kingdom Hearts where the first game aged well and the controls are still good.

Life

Persona 1 and 2. As a Persona fan I see some people saying how great they are, and the story does seem interesting, but I can't deal with that map movement, battle system and endless random battles.

Really, any RPG with random battles is a little harder to get into compared to overworld monsters you can avoid or target at your own pace.

This is a weird one for me because it often depends on whether I paid for the game. I got the first Fallout game for free (from GOG or something), and when I inevitably became confused by the UI and objective I ended up giving up on it. If I'd bought the game (either today or back when it came out) I definitely would have invested a lot more time into it, and got past that initial hump. Back when PC games came on disc with an instruction guide, reading that was part of the experience. There's definitely a awkward period around the early 2000s when games were becoming way more complex, but before in-game tutorials were regularly a thing. I find it hard to go back to a lot of those games.

Likewise I played the first hour of Resident Evil HD on my PS4 (free with PS+) and never had the motivation to get into it. After paying for it in a Humble Bundle, I played through the whole thing on Steam and loved it! The fact that I'd paid for it was able to outweigh the fact that the game was quite outdated. I guess I felt like I wanted to get my money's worth.

Any game from 2005-ish onwards feels 'modern' enough that I don't usually have this problem.

I tried to play fallout 3 and new vegas after falling in love with fallout 4 but I just could not stomach it. The games looked ugly and controlled strangely. I had more fun and enjoyment playing the original fallout from the 90s.

Lord of the rings online looks terrible but I’ve always wanted to explore.

Gta 5. Story progression is just awful. You play a mission, it ends and you're forced to do open world activities instead of continuing the story. Then just when you're getting into the groove in the open world you get a call to do a story mission and it turns out to be shooting imaginary aliens. The missions are too linear and short. Gunplay is weak. Also the characters feel like they were written for 10 year olds who think swear words are funny.

I'm hoping rdr2 is better

You'll have to sail the high seas since it requires THUG2 which isn't for sale anymore but THUGPRO is a mod that will let you play classic Tony hawk levels with all the mechanics from later games.

I'm playing through Knights of the Old Republic right now. The only thing that makes the graphics tolerable is playing on my switch. The screen is small enough to minimize the bad graphics and jank. But if I was playing it on a TV or computer screen I wouldn't be able to continue. It hasn't aged well at all.