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>RBY/GSC
I love replaying these today because I'm more aware of the sequence breaking, side objectives, and small ways to explore the games outside of the main story. Defeating Team Rocket with only 2 Badges is something I never would've considered when playing Red as a child. And Johto has stuff like the Ruins of Alph, Union Cave and Mt. Mortar which I never bothered with previously.
>RSE
Always liked and still do.
>DPP
Platinum I still think is fine, but I like it less than Emerald nowadays...Hoenn's environments keep the game vibrant, unlike Sinnoh's rugged mountains and caves and marshlands. Sinnoh Secret Bases are outright terrible since you can't remove the rocks without multiplayer. Battle Frontier has less complex rulesets. Contests are longer and I swear to god the CPU cheats sometimes.
>BW1/BW2
Loved BW1 when I played first time, but it's not as fun to replay forme because nothing about it is new or surprising anymore. This is also when sequence breaking completely disappeared from the series, so I feel like I'm just going through the motions to see the end. BW2, almost the opposite. I wasn't impressed in 2012 since I already played a-lot of BW1. But I like it more now after sitting down with it and exploring everything.
>XY
XY I loved at release, and still do. Regional Dex + Exp. All makes it fun to experiment with different party members, Pokemon I never trained in other games. Also feels like there is a-lot of "down-time" between most cities where you can sort of unwind. There's a-lot of ways to unwind too, be it Pokemon Amie, Super Training, Berry farming sim, or going back to Lumiose City for side stuff. Multiplayer is less active than 2013, but I do manage to get some good trades occasionally.
>SM/USUM
SM is like BW1, where I liked it on my first playthrough and struggle to enjoy it on repeat. I've wamred up to USUM recently for its updated boss fights and sidequests. If this had come out in 2016, I'd probably have a better opinion of Gen 7.