I think if you just take late Nov until April, Florida has better weather in those months than SD. SD has moderate winters with a decent amount of rain, it is not a warm weather climate in winters. South Florida has tropical winters where you can go to the beach and swim in the water and not freeze.
Also, San Diego has extremely cold ocean water. I live here and I never go in the water b/c it’s fridgid…yes even in summer. Unless you are a wet suit surfer, Floridas beaches are much more usable for swimming and snorkeling for the average beach goer. It’s very frustrating living in a place like SD where you can look at the ocean, but you can’t really touch it, lounge around in it and feel it on your skin (unless you are part polar bear). The sand quality is also much better in FL. When I lived in HI I swam a few times a week, in 5 years I’ve been in the ocean only twice in SD.
I do like the hills and hiking of SD though…far superior in that catagory.
Florida house prices are WAY cheaper! You can get newer house for $60k that a comparable property would be $400k in Eastlake. That is a HUGE difference. Right now you could buy a really nice house all cash in Florida and just have taxes and insurance as a payment. There are 3,000 sf newer homes going for $90k right now in Orlando.
But yes I could NOT do FL summers! And FL generally has a “lower mentaility” culture. But if you could do 6 mos in FL winters and 6 mos summer/fall in say Vermont, Maine, Montana or Colorado mountains…that may beat 12 mos in SD. Just need a job you can do from your laptop.