Typically I provide them with a mini-gift basket of the necessities; light bulbs, batteries, $25 Lowes gift card, cleaning supplies and air filters. 

With inventory the way it is, and the rising costs to build, you can't go looking at the lowest hanging fruit by buying simply distressed + rehabbing and thinking you'll be on top.

For instance, if booking for say $1,000/night (first 2 nights) offer the 3rd night for $400 since at that point it is low hanging fruit to have somebody stay 1 extra night?

The irony and karma is actually a little bit funny to a libertarian like me who got a bit of a kick out of a self described "liberal socialist" getting to enjoy the fruits of his political views.As I mentioned on your previous post, and someone mentioned in this thread, there are a-hole tenants across the social and economic spectrum. 

Just know that this larger type of risk is much more difficult and probably less fruitful than shopping for your personal home and a few rentals.  

Working with a broker you can mix a couple segments so you don't have all your eggs in one basket.

I'm looking forward to fruitful relationships and a bright, beautiful future!

Have Planted Fruit Threes to subsidize tenants and my self that continue to pay a premium in lifestyle. 2017 this year we go Solar in a big way assuring all Properties produce what they use.

If one of us is out of town, we pick it up for the other and put it in a basket in the garage.If it's within a city limits in those counties, you'll also need to call the city, to see what their rules are.  

I like the area we're in and wouldn't mind buying this house as I grew up coming here all the time and we love it, but I don't want to put all our eggs in this basket and be screwed financially in the long run.