>>20817014Lavender Town was comfy, even though it was also creepy as shit.
Viridian City was pretty good too, as well as Saffron to some extent.
Cinnabar could have been maximum comfy, but it lacked something that I can't quite put my finger on.
Also, Dendemille Town and Snowbelle City from gen 6 were pretty nice.
However, I don't have much experience with gens 3 - 5, since I wasn't terribly interested in pokemon during that period of time, so take my judgement with a grain of salt.