>>36868175Azalea is such an evergreen and probably the original comfy town/city. Sinnoh ones can also compete with it with music, colours and maps but Azalea shouldn't be as harsh in the winter. Floaroma is pretty much its sister town, Eterna City is also alright. Can't think of other regions, maybe Verdanturf (ruined by the battle tents and contests), Fortree is more known for the routes around it, I don't mind Petalburg City too.
Unova is kinda meh, both starting towns in BW2 seems fine and cozy, the others can turn shit depending on season. Not a fan of 3D cities, they can be good or comfy too like Snowbelle or Courmarine but I find the 2D maps more charming and fascinating, especially Gen2 and Gen4 ones and the 2.5D Gen5.
Lando has been always horrible at maps, easily some of the worst towns map wise, Pewter City perhaps can get a pass, for Tokyo, Saffron and Celadon had to put more efforts in those copypasta buildings. Lando only got better looking thanks to Gen4 tiles and colours giving it a more alive feel but even this didn't fully save it, LGPE maybe made it look cuter at least.
Shoutout for Jubilee City for the big cities candidates