@Tim Simmons No, we don't typically give the house captain a discount, but we've started to give them some type of gift card if they're doing a good job communicating.

Just do it, tell them to send you some gift cards for the inconvenience lol otherwise they might have to call your note if its in their legal reach. 

You can even gift back her rent to her with your annual gifting limits.

How big of a gift can he receive from me for a down-payment?

All the other economic and "do you feel safe" criteria seem intricately linked to crime. 

We bought cars for single moms, dug wells for orphanages, bought gifts for AIDS camps in Jamaica and in early 2008 we were both told to give it all for 6 months to a couple we had known for a long time who had suffered some catastrophic setbacks. 

I think this is the gift and the curse of a still emerging asset class (short term rentals) - as it becomes more "institutional" i.e. more like commercial real estate with more sophisticated buyers then financials and systems for this will likely become more streamlined and stable, but we are still in a place where the buyer pools are more newish investors or typically residential basic investors, so not has experienced or sophisticated evaluating investments based on a detailed financial analysis like more seasoned commercial investors likely would.anyways, just a guess on what might be going on here

The only thing you can safely give them is a "gift" of merchandise not to exceed $50 in value.

Google Kumulori.com to see book.Is this a good type of local gift product for Airbnb and hotels?  

Then when the property is sold, she excludes the entire gain as a sale of her personal residence ($250,000 exclusion) and she then gifts you the proceeds (nontaxable) saving all of the tax with no 1031 cost or deferred taxes.Just sayin . . .