[Remed]

My two goals are to maximise my disposable income and to get to know people who could improve my life (by further career opportunities, by being good cofounders in the future, or simply by inspiring me, being worth talk to or learn from). The second goal is hard to achieve when working remotely (I used to work remotely for several years). The first goal: I know that SV is an expensive place to live, but I have an impression that companies hiring remotely pay so much less than SV wages, that even considering cost of living you can save more living in SV.

I had some roller-coaster in recent years and I need some peace of mind for the next few years. What I mean is to work for a company which most likely won't go under in the next 12 months (hence "reasonably well funded") and with enough resources to get things done; and kinda to focus on one area rather than having to take care of everything and then more. I don't mean I'm looking for a low stress job. Just a bit less stress, bit more certainty and bit less responsibilities than when running/bootstrapping your own company (I did that in the past and will probably do it again, but in a few years).

[brudgers]

It sounds like a more established company might be a better landing place. Established companies are probably more likely to accept the risks associated with relocating someone in their forties and have more experience with doing so. Those companies also are less likely to go under and large companies offer more opportunities to meet people.

In the end, if you want to move to California, decide to move to California. Make the tradeoffs. Figure out the details. Work through the problems. If it doesn't work out, it doesn't work out.