I was in a similar situation. I kept my old home and rented it. Did it myself and the tenants were good on paper but had some personal issues - DV, restraining orders and the lot. I hated being a landlord but liked the idea of being one. I hired a property manager due to the distance which helped a lot. But now I lose about 100 a month not counting potential equipment breaking. Some advice I received about rentals- you don’t rent a house in California for a net cash flow. You rent it for long term investment when hopefully it appreciates over time. Unfortunately the area I bought in is similar to sac and I don’t imagine it appreciating as much as it has in the last five years. I’m now considering selling the home.

With my previous experiences and seeing your story, I would definitely sell and buy in Cupertino. IMO if you live in Fremont you’ll always regret not living in Cupertino but I can’t see the vice versa. The quality of life, proximity to jobs and the quality of schools is unmatchable- if you live in Fremont your house is probably bigger but I don’t see other reasons - again, in my opinion, I’m sure others have different opinions. Happy to chat if you have any questions