In my personal experience remote work does not work so well. At least I haven't been able to make it work for me.
For the second point, well I think expensive cities are expensive because people want to be there. If you can choose to live anywhere, why not go to the best place, specially when you can afford it?
I've worked remote for almost three years for a profitable startup. It's not all sunshine and rainbows, but not having a commute is incredibly liberating. I've also found my careeer options to not be limited by being remote.
Also, I live in Florida 20 minutes from one of the best beaches in the country. Not as "culturally fulfilling" as say the Mission or Castro districts (have been to SF more times than I can count, but have never lived there), but I sit on a quarter acre lot with a 2600 sq ft 4 bed/3 bath single family home with a backyard pool for ~$1000/month (owned, not rent).
Trade offs. Living in expensive cities doesn't necessarily translate to a higher quality of life.
That sounds great! I'd move back to Florida in a heartbeat if I could. I used to live on the beach for chrissakes. But it sounds like a tremendous risk. You're betting that you're always going to get to stay with that company that allows remote work, or that you'll be able to find another one.
I've done a tech job search while living in Florida--not pretty. It goes like this: Company's hiring manager: "Move to the Bay Area or GTFO." I eventually had to do it so here I am.