Yes, don't know exactly when (I think it was a gradual thing), but I'm aware that a lot of the reasons for enjoying retro gaming is not related to the actual quality of the games you played back then, but about the context of the time they were released and what they meant to you.
Personally, when I'm playing a retro game or messing with retro computers, I tend to put my mind in the context of the time of such game/computer. I try not to compare it with things that came after it and instead compare it with whatever was available at the time.
In the context of graphics, I'm far more impressed by older games that uses its base hardware very well than by any current AAA game. Yeah, today games look "better", but the fact is that most of the work is being done by brute force by the hardware. There is less and less creativity involved and a lot of games look the same as they all tend to look photorealistic.
Games back then were more contained, and thus more "personal", it was usually made by fewer people and the result was more personal, even if they were working for a company. Nowadays a game is made by hundreds of people, working for a company that decides how the game must play and look like. Its almost like comparing a painting or sculpture (much simpler, made by fewer people, but more personal) to a plain building (lots of work and people involved, but boring).
There are the indie games as well, but even those don't impress me simply because they aren't actually limited by the hardware. It's not the game's fault in that case, but mostly mine as I like observing what people can do with the console or PC limitations.
Another reason for enjoying some retro games, even without putting myself in context, is that they have some gameplay mechanics that are not used anymore which I enjoy, like allowing you to lose the game: Really, which modern game allows you to truly lose? I mean, not just returning to some checkpoint, but having to start from scratch?
Nowadays a game like this would be bashed for being "too frustrating", so every current game is kind of forced to give you some safety net that will never let you go back beyond a certain point. It may have tough enemies or an almost impossible boss to beat, but you only need to do it once and never again (unless you want to) as the game will "lock" you past that point forever.
Recently I played the first two Tomb Raider games from start to end, and part of the fun was being able to master the character movement: You had to learn how to run, jump, walk, look around, sidestep, roll, draw weapons and learn the appropriate time to use each movement. Current games usually have a "context button" that does whatever is required for you, plus, there are lots of invisible walls preventing you to do anything stupid (if I want to swan dive head first in concrete, just *** let me, damn it!).
My first disappointment with gameplay becoming automatic was with the first Assassins Creed (I hate the series, as for me it embraces all things I despise in gaming industry 🤣). After playing the great Sands of Time trilogy, I wanted to see the game that succeeded it, and then this boring POS came... the character was doing many impressive things on screen, but in real life I was just holding a button and moving the stick to whatever direction the character was going. Then the combat consisted in waiting an enemy to perform a telegraphed attack and press another button to win, I tried to play the second game, but got so bored I couldn't get to the end.
Athlon Thunderbird 750mhz
256Mb PC100 RAM
Geforce 4 MX440 64MB AGP
Sound Blaster AWE 64 CT4500 (ISA)