I rewatched the first season not that long ago and it still held up well to me. I always felt that at least in my circles as a kid, Digimon got the bad rep of being "Like Pokemon but worse" but I always felt that the anime was significantly better and more emotionally resonant than Pokemon. As much fun as I had with Pokemon, every episode had a formula of Ash wanting to be the best trainer, yet still not knowing basics such as fire being weak to water and Team Rocket with some shenanigan that had to be stopped. Digimon S1 had a much more engaging story with the kids being pulled from their lives and thrown into a mystery world. All the stuff they went through and activating their crests and growing as characters, it's a lot more interesting and a big reason I still enjoyed it.
Beyond S1 though I felt like S2 was a slightly more mixed bag where it's the common movie sequel dilemma of, "Its kinda the same but not as good" and some of the changes or new things they introduced didn't work as well for me. But I can still enjoy it. But beyond S2 I haven't quite gotten into much else. I will say the anime seasons beyond S2 did do some interesting choices and I applaud that but it also got away from what I liked so much with S1.
On a side note, I had a ton of fun with the PS1 game Digimon World back as a kid. Could never beat the game due to my Digimon dying eventually before they got strong enough to take on the final bosses but I still had a lot of fun and I grinded so much in it. I was really happy to play Digimon World Next Order a few years ago and all the nostalgia came back. Not sure if this one was easier or harder than the old PS1 game but I did manage to at least finish this one and all that's left is the post-game content which is very grindy and I have not finished. But I think it's awesome with games that leaves a lot of content for you to do (if you want) after you beat the story.
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