My brother and I are right where you were starting out—hope to be in your shoes someday!

However it appears to me that the three dovetail into one another.

That is, buying in my personal name and moving it to the LLC after the fact would essentially nullify my title insurance.So, it appears that if I want to preserve the title insurance, the way to go would be to either do it the way I did it previously (i.e., LLC to personal name and then back to LLC) or go with the land trust option that you suggested.

The last bullet of the San Diego County Zoning Guidance document (Link) appears to state that this type of Airbnb listing is not permitted.

Vacant buildings are common and affect the appearance and quality of the city.

As a result what appears to be a liability to the landlord can be an asset by keeping the tenant put !

Other companies also appear to be the same price. 

How bad is the appearance of those properties? 

@Evan Evans to all saying you can leverage cash for great deals- you can also use lines of credit to close quickly or (at least in Missouri) check the box on the Purchase Agreement that says “not contingent upon financing” to appear as a cash offer.

You need actual steps, that are practical from the perspective of someone that has been in your shoes, that remembers how hard the struggle was, that knows how difficult it was to break through the analysis paralysis phase, that made mistakes, learned from them, and can predict where you will also stumble and fall and give you pointers when and where to be extra careful.So if I have convinced you that I know what I am talking about because I HAVE been there, this is what you do, knowing now what I wish I knew then.GET A WEBSITE!