I sort of did a variation of what you are proposing. I lived in a colder climate and bought a condo in San Diego (on the Point Loma/Ocean Beach border. Luckily, bought during the downturn). Before buying, I rented short-term houses in PB, OB, Point Loma and Mission Hills at inexpensive rental rates. However, this was before AirBnB, and doubt those kinds of deals exist anymore.
Like you, I have work that allows me to be mobile. But now I'm a full time San Diego resident
During the winter, I would rent out my other home, which I owned, to visiting nurses or other short-term renters. In the summer, I would rent out my condo in San Diego. There are people coming out of the desert who are looking for a rental in San Diego in the summer, so there's that. So you could conceivably find a way to rent out your place, though with the crazy market as it is, it may not come close to covering expenses.
In our neighborhood, there are places that almost fit your parameters, like https://www.redfin.com/CA/San-Diego/495 ... me/6671211
and https://www.redfin.com/CA/San-Diego/440 ... me/5351579
. There are others even less expensive (smaller). Of course, the flight path impacts this neighborhood to a varying degree. But it is an option.
I will say that it was tougher emotionally to split my time, leaving different sets of friends behind each time. And eventually I found myself in a relationship, and needed to live in one place. For me, it was different, as I realized that SD was where I wanted to be full-time, and eventually made that commitment after splitting time for a few years.
There are taxes for your business, but on the business side all that means is that you'll likely pay is the $800 Franchise Board tax and nothing more than that. If you are incorporated, you may need to register as a "foreign corporation." It does create complications in splitting taxes across states unless you are in California for a short enough period (can't remember what triggers part-year residency).
So it's tough. I would lean toward renting, especially given the fact that we're at a peak in the market, and uncertainty for you on how things will work out. You may try it for a year or two, and decide it's not workable. I'd make sure this arrangement makes you happy first before committing to buy.