I came here from LA in 1991 to attend UCSD and have spent most of my time here since then but also travel quite a bit (the longest being a one-year stint in Tokyo). I bought my condo in SD in 1999. Tokyo is like home to me, I speak the language and accumulated over 5 years traveling, working, and schooling in Japan. Nothing can even come close to the numerous things you can do and see for free in a country which is smaller than half the size of California. When my friends or family visit San Diego, I am ashamed to not have anything to do besides take them to the beach (we’re not Sea World or Legoland types) but that gets boring quickly.
I like Tokyo because I’m very much a city person. I like active, vibrant places with a pulse. To me San Diego is flat-line. I spoil myself every year going to Vienna for Opera (it’s not boring when you see it as it’s supposed to be). I collect art. Balboa park has very little of any interest, it’s more of a strip mall with some mildly interesting architecture than anything else. The museum exhibits are decrepit relics (as opposed to fascinating antiquities). I see better displays at granny’s house.
Chicago is superior in food, parks, and museums, as is New York, L.A., San Francisco, and Boston to name a few. If you like clubs, pretty much anywhere is better than SD (I mean come on, how many pseudo-salsa dance places or techno-trance-hip-hop clubs filled with drunken white people do we need in the gaslamp?). I’ve tried all the jazz clubs, no thrill there. Comedy? Lame (Avenue Q was nice, but it’s from NYC). Restaurants? Nope. I think all the cooks in SD were trained by the Denny’s master chef (unless, of course, you go high-end). I went to a restaurant that called itself Indian (downtown) and it was blond-haired waitresses (I think they also came from Denny’s) with bindi on their forehead serving week-old bread and calling it nan. Most sushi places here serve Korean versions of Japanese food but SD folks don’t know the difference as long as someone yells irashai when you walk in.
I have so much to write about but don’t want to overdo it any more than I already have. Just to answer your question cities I personally find superior in some ways are:
NYC
Vienna
Tokyo
SF
Chicago
Boston
Budapest
Like you said, SD is all about the weather. The places I listed above don’t fare as well in that respect and don’t have proximity to the Pacific (though I am an avid snowboarder). For me, it’s also about the money.