Do you have an idea of your strategy for getting started?

Taking in the content sounds like a great starting point, and teaming up with someone experienced in these deals is a fantastic idea.

--reach out and thank them upon getting the booking and ask if they have any questions--send a "Welcome" email or automated message during the week prior to arrival--reach out the day after arrival to ask how everything was the first night and ask if there is anything that the property needs--reach out at the end of the stay (that morning or within 24 hours) and ask how everything was, anything to improve, anything to add to the house and then offer an incentive for returning guests.My 2 cents,Mike Absolutely stay in your place as Mike said.You will see things the cleaners will never let you know about.We stayed in our PF will putting up the Christmas decorations and found a cracked plastic shelf in the fridge. 

I'm in the same boat for reference- I bought into the "buy now, refi later" idea and am sitting on a 7.375% on my latest property acquisition and a commercial line of credit I have is at prime + 1 (so 8.5%).

.: Any idea how far south the potential for Santa Ana or similar winds goes?  

I guess the idea is to use the equity from one property to purchase the second property, and so on.

I think all of your suggestions are great possible ideas to do this deal! 

Just ideas, talk to your CPA to make sure you are doing it properly. 

The idea of real estate investing both intrigues and terrifies me.

It will at least give you an idea if the PMs records are way off what you think they should be.