The only real issue was all the fake ways to get Mew and the awful greedy Nintendo marketing department that removed Mew from the American game so that you could only get him from sanctioned events. What made it even worse was that they would look through your Dex before giving you one and if they saw you had used a GameShark or a MissingNo hack they would deny you the transfer.
Personally I found Diamond to be the magical experience. Everything I hated about the game I loved had been fixed. It was in color, there were no stupid cables needed that nobody had, and you could easily trade and fight over the internet. I was also old enough to know that a game can be more fun without looking at the guides.
Gold was like everything I didn't know I wanted, with cool new Pokemon and then the amazing "reveal" that after the first 8 gyms I could go back to Kanto and basically play through the Gen 1 game as well. I had no idea that was coming and it just blew me away as a kid. Tons of great memories of that game.
I didn't get into the next generation for whatever reason, just kinda missed me.
But Diamond was also fantastic. I had three other friends with copies and we would just sit around playing battles, hunting shinies, and just overall enjoying the experience together.
Those were the only two Pokemon games I played and they were both such peak gaming experiences that I'm barely interested in the rest of the franchise. How could anything top being 9 and deep diving into Gold, or being 15 or so and having a whole group playing together and just drinking mountain dew all night? Those games hit at the perfect time for me and I don't see how anything new for ever exceed those experiences.
Everything procedural in nature essentially reflects the design philosophy of the creator: that's a fundamental restriction on the Holodeck. The generative approach is actually creatively less productive than a chaos function, because chaos is known to produce interesting long-run patterns, while generative acts more like an interpolation on existing patterns.
[1] https://en.wikipedia.org/wiki/Pok%C3%A9mon_Mystery_Dungeon