It sounds like your intuition is guiding you in a particular direction and you want confirmation from us it's the right move :) It's probably the right move for you. Only you know. I've been in the bay area, renting, with no roots or attachment for 15 years. I've had a lot of similar feelings. Also working on my own stuff income free and not planning to work for tech companies here. What keeps me here is 1) not having another place I want to be 2) cheap rent ($1800 kitchenless studio) and 3) not being in the city (palo alto). if any of those 3 conditions changed I'd probably be out of california at least for long enough to decide if I want to ever come back here for good.
FWIW: I paid that for an awesome 2-bedroom with dedicated parking right on University Ave about a block from Middlefield 2009-2012. Now that's like half of my mortgage for a house that's about equivalent to the average homes in that neighborhood... But in a different state.
At the time I had a great roommate, so my real cost was about $900. Given the nature of what I was doing, I wasn't going to eat Ramen noodles to chase a bootstrapped pipe dream.
I ended having to go back to work for health insurance. (I had a pre-existing condition and the ACA hadn't kicked in yet.) Otherwise, I would have pushed a few more months.
(I knew my business was a pipe dream walking in, and I knew I was starting it for the wrong reasons. At the time I had some emotional needs that I needed to satisfy, and unfortunately I didn't seek out the right resources to plan what I was doing.)
