And in the US and much of Europe, school and general vacation schedules play a role as well. September and October tend to be really good times to visit a lot of places that are packed in July and August--and the weather is often even better. Get into the winter and it's at least a different experience out of doors and may not even be really doable for the casual visitor (though of course cities are always visitable to some degree).

Exactly, that’s generally my tact on my digital nomad adventures… try to avoid peak season, but don’t go in the middle of winter/summer in a seasonal area