To me the quadplex would be dual purpose, while you are not living there it serves as a reliable stream of income, once you move there, you could live in 1 of the units while you build your permanent home, and you could also use it for when your family comes over for large gatherings.A 2nd option might be to build an RV park, Unless their are zoning restrictions, you should be able to build one fairly inexpensive, with a septic system and either public water or a well, you can keep your costs to a minimum by doing gravel roads, which are easier to remove later if you don't want them. 

Here, you should be obtaining a geotech report and reviewing the title report and the zoning  to verify there are no deed restrictions or zoning overlays. 

The local markets depending on where are talking about or have put in restrictions on STR's.

I’m aware California is not the best market, with the restrictions and potential new tax coming up, etc, but we have personal reasons to invest there.With that said, we visited a lot of houses in the San Diego area and saw 2 that seem like a potential fit for us: one is a smaller 3 bedroom but a mile from the beach and the other is a 15-17min drive to the beach, but bigger with 4 bedroom and a little cheaper, which would allow us some cushion to invest on a hot tub or potential pool.

@John Mason yes, but I am sure some of the condo associations probably do not allow them or there are other restrictions.

Thanks all.Yes, my tenants will cover the appliances according to my new contract; it will be up to me to see if the tenant is worthwhile to pitch in.I actually already have this clause but I will tighten it up a bit.It may look silly but the new appliances are so expensive I am not willing to buy premium appliances every 5 years for my A class properties. 

I understand the restrictions in the market (and that Napa county in completely restricted) but and am hoping to find an agent with experience specifically in short term rentals in the Sonoma market.

Then I expect more stabilization in pricing and less concessions as the market will tighten as we get a 2nd rate cut in Q1 of 2025.

So we have had zoning changes in parks we have owned and they can put huge restriction on your property.

Even though I will most likely win the case with my own funds fighting it, all three insurance companies found language in the contract that disqualifies coverage for this type of event.So I dont have faith in most insurance companies - they all seem to tighten up when claims are filed.