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Replay value

The first five, but probably 2nd generation I replayed the most times. After XY I think the games got dialogue heavy. Also I love the sprites!
 
While I play a lot of games in the Gen I to IV department, the ones I play the most are Gen I and II.

They're just so easy to crank out a quick run - thank God for turbo. I could include Gen V here but it's attempt to do cinematics and story heavy when I'm interested in neither of these things - and in fact, actively hate in some instances, looking at you Hugh - make me lose my interest pretty quick.

From an art standpoint, ORAS and the Alola games are definitely pretty games which I do love. Unfortunately I'm so used to turbo that playing Pokémon without it feels so ungodly slow.
 
HGSS for me. They just offer so much in terms of content. Plus having the two regions expands gameplay.
 
Probably don't have the time and resources or something to regularly include two regions in the games. For a whole decade the games (or the initial pairs at least) have felt unpolished, so it's hard to imagine that they'd be capable of doing it (or doing it well) multiple times.

Or maybe they're afraid that it'd be stale to do it again, or that they want to focus on one region at a time to make it feel more special rather than have regions share the spotlight or something. Maybe G/S/C was just a special exception since they were the second games and Pokemon was still new. IDK if there's any way to know really.
 
makes me wonder why GF hasn't yet made another game that features more than one region, considering how succesful & enduring these titles have been

Well, the obvious reason is that Game Freak thinks "kids are dumb and have the attention span of a fly. why bother adding a postgame they won't play?" (which is coincidentally, the same reason they're making the games easier). This was confirmed by Masuda in an interview when ORAS came out.

Until Game Freak decide to actually try and understand what their audience wants - which is unlikely considering Pokémon basically prints money and Sword and Shield sold more in the early days than any other game* in the franchise (with a higher price) - it's unlikely to change.

But even if that weren't the case, I think you might be confusing correlation with causation. It worked in GSC because they were the second games after RBY so it was essentially a throwback. And HG/SS works because it's a remake of GSC.

If they tried to do this with say, Galar, do you think the people would be saying "Two regions, nice!" or "Why did they try to do two regions instead of working in National Dex / graphics / game difficulty? What a terrible management of resources!"?

*although to be fair, these numbers need an asterisk since videogame sales in general - and Switch games in particular - rose drastically due to the pandemic
 
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