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After mulling it over a bit I've decided on
Kanto-- Pallet Town? It's hard to pick because nowhere really stands out to me. I'm fond of Lavender but I don't think most people would describe it as comfy. Confession: I've never been to Mt. Moon Square, maybe I'll dig out my HG and check it out sometime
Johto-- Also hard to pick one but for the opposite reason: comfiest region. Lots of good places to choose but I'm going to go with Ecruteak City. The music soothes my soul, and I'm a sucker for Japanese style buildings
Hoenn-- Pic related. Route 120 at night is one of the prettiest areas in the entire series. Thanks, ORAS
Sinnoh-- Like Johto, also has a lot of great locations. Personally I love forests, and Eterna does not disappoint. Quiet and serene, with just a touch of spookiness but you know that you're still safe. As long as you don't approach the mansion, of course
Unova-- Virbank, which is weird as I'm not really a city person, and I get the impression its kinda run down and grungy on top of that. But something about it just sits right with me
Kalos-- Route 7. Colorful flowers adorning one side with a river on the other, what's not to like? Reminds me of some places I visited as a child
Alola-- Honestly I don't remember much of the region. I felt like I was just a tourist, being shepherded from one spot to the next without much time or reason to go off exploring on my own. Memorial Hill I guess? I've always found graveyards to be very peaceful