I've spent the last few months in SF considering moving here more long-term. I have a remote gig in tech so I have freedom over where I live. Before SF, I've been in NYC, Boston, and Milwaukee. I prefer an urban setting and prioritize running. I spent a ton of time reading up on living in CA/SF before jumping to come out here so I had heard of many of the pros/cons. Now that I've had a chance to experience living here first-hand, I've basically found it all to be true. Even seemingly contradictory statements tend to be true. What I've found:
** Running **
Some of the most breathtaking running routes in the world. Golden Gate Park, Lands End, Ocean Beach, Marin, etc. Trails on end. You'll look forward to your weekend long run. I've started to realize how much there is out there and how far some of these trails are...I never really understood trail ultras but now I do.
So it should be god-level running, right? Somehow, no. Day-to-day running is just as annoying as anywhere else. It still gets dark at 5pm here in the winter and the places you want to run are very dark. You'll want a headlamp even for the main streets in Golden Gate Park.
I'm lucky enough to live a half mile from Golden Gate Park. Ideal for runners, but if you happen to end up in another neighborhood (let's say SoMA, so you can walk to work) then you're basically confined to the Embarcadero or having to travel to the place you're going to run (something I refuse to do on a daily basis).
I think Boston is a better city for day-to-day running (i.e. just step outside and start running) while SF blows Boston away in terms of access to trails and interesting destinations to run within a 60 minute drive. SF's still probably the best all-around city for running that I've visited, but...
** Cost of living **
Yep, it's outrageous. It makes sense given the weather, scenery, and high-paying jobs. But even then, it seems to be really out-of-proportion right now. Housing is the main cost. In SF it's tough to find a 1BR for $2500 right now. Houses are $1M+. Ok, so just move to the burbs, right? Nope. Silicon Valley to south is where all the tech companies are and everything's expensive there. The East Bay (e.g. Oakland) is slightly cheaper but anything "urban" around there is really rough. You can probably find a suburb that's not rough, somewhat "cheap", and livable. But wait, I wanted to live in an urban environment...
I understand market dynamics and why prices are where they are, but for a newcomer coming here looking at $1.5M houses or $3000 rents which would be like $250k / $1000 in the midwest, you really have to consider if it's worth it anymore. If you can pull down the same or similar salary in the midwest, it's gonna be really tough to justify that 3-5X housing cost increase.