I live in Michigan and work for a company in SV. I love it in general but feel like it's pretty unlikely that I'd be able to find similar situation if I were to lose my job. It's not the best position to be in.
I'm also looking into diversifying income streams with some seasonal side business in an effort to capture some of the tourist dollars that flow through the town.
My new goal is to buy up as much of the town as I can, I now see contracting as an income source to park in more rental property, and thanks to the magic of leverage and anticipated low interest rates, this should be a viable exit strategy in relatively little time.
I live in Southern California, but not in San Diego or LA where the prevalence of some sort of other tech work might be somewhat possible. Instead I live in Imperial County (bottom right of California).
Here, all of the decent paying IT work is in the County, State, Federal jobs available in the area, but this doesn't really represent Programming/Development work very well since those are even fewer amongst these organizations.
There are no real private software companies and while I'd like to start something on my own and go full time down the road, there's still tons of gaps in how that would look, and potential financial risk.
So where I'm at right now locally is really the best place I could be in.
But...I worked at eBay in San Jose for a time and I had two coworkers, one who aws a UX guy who worked out of Austin and came into the office about once a month in San Jose, and the other was a developer who didn't want to leave Australia so they flew him in every now and again too.
I really wished at the time that they could offer something similar to me, allowing me to stay down here in Imperial County (mainly to be close to family) but still get to come up to the Bay Area and work in the office every now and again (a nice mix of both worlds).
On the one hand, I haven't gotten any job offers from any companies lately, but additionally I would have the same concern as jphillipsio...if for whatever reason the company that hired me and allowed me to work remotely decided to let me go...how easy would it be to get another remote job with another SV company? If that didn't pan out, what would be the likelihood of me getting anything remotely similar locally?
Lot of things people have to worry about in these situations. Stability isn't always important...but it definitely becomes a big factor once you have a family or other responsibilities you can't just easily stop providing for.