Hey Geoffrey,Where do you live?

But I can't if closing costs are 3-5% for purchase price of each home. 4) How do I protect myself and give the seller assurance from renters with the structuring of the home insurance?

I do not want to be cruel and want to give heads up for a future time period. 

Nashville is a competitive market and to find deals you really need to do some work.

Even if you create a non-CA LLC, if you are managing the business from California, you will likely be deemed to be "doing business" in California and therefore likely subject to CA taxes.

@David CianciI do not know the details of your business, so it's only a generic answer that may or may not apply.

If he keeps living here for several years, do the deductions roll over year after year an accumulate? 

Best best is to call a broker and they should be able to tell you what to do.

Seems like Google doesn't partner with AirBnB like they do VRBO, booking.com, and others so that means my property won't show up as a vacation rental with the "check availability" booking link on google maps or google web search. 

The downside of trying to get a mortgage after you have a rental is that you can't walk into any bank because they do not understand how to calculate DTI correctly.