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"I can replay this forever and never get bored."

Emerald, Platinum and Soul Silver are the three games I find myself replaying the most often, as well as Explorers of Sky and Shadows of Almia if you include spin-offs in this.

I used to replay Pearl often until I bought Platinum. Later gens aren't as replayable imo, though Scarlet and Violet could have easily been much more replayable if they had level scaling.
 
I've been playing Gen 7 every winter since it released. It's comfortable to me.
 
Yep, with pretty much any Pokemon game that lets you build your own teams. There are so many potential team combinations that I don't think I'll ever get bored with the series.
 
When I replay older games it's usually gen 1 and 2. Occasionally, I also replay gen 3 games (Emerald usually). Gen 1-2 are just very quick to get to the gameplay. Gen 3, Emerald especially, end up being somewhat slower (all these people randomly showing up to give you their number <_<) but still fairly quick.

On the other hand I just can't find myself going back to gens 4 and 5 due to how slow they feel at times and generally I don't really have access to a DS/3DS, anymore, as well.
 
The Hoenn GBA games are like breathing to me. I can knock out the main story in a day or two if I'm just running through it for the sake of it. As much as I love most of the mainline games, there comes a point where I feel I need to take a break because I feel tedium from the nonstop playing... that doesn't happen in Ruby, Sapphire or Emerald though. I think it's a mix of game feel and familiarity, and I wonder if other gens could join them in this way if I play them more.
 
I think i can replay amount of times generation 3, because they are so nostalgic for. This games were my first introduction to this franchise, so they are my favorites for that reason
 
I'd say Fire Red/Leaf Green, Emerald, and Heart Gold/Soul Silver are like this. Those are the games I remember the most out of nostalgia but also because of the set piece and challenge. Not too easy but not too hard.

Black and White 1/2 aren't bad but I only played through those games once each. Never finished my second playthroughs.
 
Not really, I love HGSS, BW and B2W2; but I definitely have to take 2-3 year breaks between playthroughs of them for things to start feeling fresh again. I prefer to just spend a ton of time on 1 save file and try to complete all the end game content.
 
OG Red is the one video game that I have replayed the most in my life and I always end up replaying it at least once a year.
 
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