Personally, I am not a big fan of STR's although they may be fantastic in certain areas of the county.

I started almost a year ago..its been a journey but no horror stories...yes drama but no horror...the person I was considering hiring to oversee the project decided to take the project on which was a dream come true...thx for your advice ..i did what you advised and then got lucky!

Personally, I like that it’s a bit more spread out and the views from the pool areas are very nice.

You might want to explore STR tax strategy if you are finding that the long-term rental tax strategy isn't working for your personal situation...

I personally develop quite a bit in a neighborhood where the zonign laws are already quite prohibitive and to make matters worse, the community as a whole fights all housing from being built in the spirit of stopping gentrification.  

Access to an STR isn't essential, but helpful and bonus when it's personal usage time..- Insurability & Operations costs: Can be considerably lower (especially in comparison to CA) with most coastal regions there is much lower wildfire risk and the properties that are in flood zones, have surprisingly accessible and affordable policy costs.

There's some complicated ways around it and things may have improved, but I can tell you that I was personally threatened with being charged with a felony in 2019 for renting my property even though I had gone through the proper permitting.

My thoughts: East Bay:- Close to a BART station to traveling medical worker/corporate person could hop on a bus/BART to work: El Cerrito, San Leandro, Hayward, Fremont, Walnut Creek, Pleasant Hill, Concord, Dublin, Pleasanton- Maybe Richmond, Antioch and Pittsburg but some parts have a lot of crime. - Going further out Brentwood and Oakley have appreciated quite a bit and have pretty good schools- Something with potential to add value: ADU attached to the main house or separately in the backyard in the future to get additional rent.

I use a broker, they do the leg work and since their interest is in my success, as opposed to an insurance sales person who's only interest is making commissions.

(And best case it was a rental for 17 years then a primary for 3, making only 15% possibly eligible.)Personally, if you and he are both 100% sure of the facts I would first reach out to a qualified intermediary (a person who handles 1031’s).