Hmm... I'd like to be somewhere with a little bit of a chill in the air, either by way of cold temperatures or a strong breeze. I don't necessarily want to settle atop a mountain, though, as I wouldn't care for the climb. I don't want to be too isolated, either. What if there's an emergency, after all? Given that, I think we can eliminate somewhere like Fahr Outpost or the area around the Enigmansion. I suppose Shiver City isn't a bad choice. There's a Warp Pipe connection right to Toad Town, after all. It might be a little bright there with all the snow, though...
Let's see... considering some other options... There's Twilight Town. Perpetual twilight means it shouldn't get too warm, and it's not that far from Rogueport. It'd be a simple, quiet life, and I'm partial to that idea. I could go investigate the Creepy Steeple, maybe document it in a book. Although... getting through a forest with Amazee Dayzees sounds... difficult. I doubt I could make it out to the steeple. It's such a small town, too. Gossip spreads quickly, I'm sure, and the Twilighters already seem... less-than-fond of outsiders. It might not be a very welcoming community. Plus, while city access is nice, we're talking about Rogueport, so... maybe that's not the best choice.
If not snow or darkness, maybe the sea... I do like the idea of living in Noki Bay. There are few rocky beaches where one might build a house, and the abundance of history excites me. I could spend my days learning about Noki culture, basking in the sea breeze and the shade of the cliffs. On the other hand... we're back to climbing, and that's not going to work for me.
Rogueport is unsafe, Delfino Plaza is too busy, Gelato Beach is too hot... but perhaps Port Prisma would do. It should be somewhat cool, being by the sea. If the newspaper-reading Toad and the cafe are any indication, Port Prisma offers a relaxed lifestyle. There are major facilites like a post office and a museum. I could see myself sipping on a beverage in Port Prisma. Temperate and moderated by the sea breeze, lively but not bustling, with wide open plazas and streets...
Yeah, I could settle there happily. I suppose I would head to Port Prisma!