Remember a good plan executed now, is better than an excellent plan executed later.  

Here are some of the most commonly requested items, not an exhaustive list: Social security number Proof of employment.

From your posts it sounds like you are thinking more like a homeowner than an investor.

Buying and renovative a $800K home might not be achingly more difficult than an $80K home but downpayment, holding costs, etc. are astronomically higher.  

The good news, however, is that you will always get cheaper financing for a primary residence than an investment property, independent of the fact that you bought it after an investment property.Julie

A mortgage helper any which way you slice it can add more value than an additional bathroom depending on the area.  

That said, you'd probably still have people that would choose the (net) $545K because they can get more than an 11% cash-on-cash return.

It SOUNDS LIKE you want to create something closer to a Zillow or Redfin where people can come to you directly to list their property rather than an agent.

I realize in the end, I'll most likely never get my money back, but I'm going to exhaust every avenue possible, regardless.  

@Michael ElderI wouldn't mess around with anything other than an insurance policy tailored to short-term rentals.