I moved from SF to SD about 5 years ago. SD definitely wins on climate, less traffic, lower houses prices. But SF and some other areas of the Bay to me are much more interesting places and “higher mentality”.
A lot of SD has a lower mentality crowd and a lot of directionless uneducated people. I think the general population here have more in common with say Texas or Arizona in style, taste, mindset vs. SF/Boston/Seattle/Manhattan (and I don’t mean that politically). It is also more “commercialized” and has a lot of unsightly suburban/cookie cutter, sterile, characterless areas (like Rancho Penasquitas where I live now and most of inland North County IMO). These areas are just totally car culture mall oriented places, you never see anyone on the sidewalks! They are so sterile feeling and devoid of any uniqueness. There are only a few places in SD which are kind of cool, interesting and have some character (parts of North Park, Univ Heights, South Park, Hillcrest)…and even those areas can lack.
SD is blessed with the best climate in the world, a very cool landscape with mountains/desert/ocean, not bad traffic for a city it’s size, and much cheaper housing than SF (and NYC and close in Boston too). And those are VERY strong points. I would give climate/landscape an A+. But I would give the *city itself* a C and the architecture maybe a C- and the quality of people probably a C-. Think about it, people live in Seattle and Boston and love it even though the weather sucks bad. They tolerate the weather because the cities are cool and have character. Would ANYONE live in SD if it had Seattle’s weather? No! It would be an ugly place w/out the sunshine.