I think as you decide and analyze the content David Green has put out recently about “return on equity “ is worth considering. 

Problem is you either have to be very right in your predictions, or have lots of cash in reserve, because otherwise the “alligator’ may eat you alive! 

I have read David Green/Brandon Turner's books but am having trouble figuring out the logistics of managing a an oos rehab. 

Or is it your place, is it just too downscale for the rent you are asking for it.What if the rent was $250 a month--would they still flee the area, or would they sign on the dotted like.If it's not price or product, then maybe you are attracting the wrong prospects to the place.People who eat too high on the hog---birds of a feather--sort of thing.As a New England financial consultant I'm assuming you are pretty far removed from the possible renters in this area.If the area is really tough, can you read gang graffiti and discern it from tagging?

Then you’ll be out pretty little cash (be mindful though that you’re going to have to be slightly more flexible on what you want cash flow wise because your loan is going to be eating up a lot of that).

Greene.

Using that same "logic", if the people that rented out those short term rentals through out the food they didn't eat in the fridge when they left, how many people could that food have fed if they didn't waste it?

Because new cars eat wealth and drop in value 'like a rock', I would never recommend going that route, especially for 'tax benefits'.   

I grew up in Illinois, used to live in Chicago and used to tutor kids in Cabrini Green, I have a little understanding of the dynamics of Chicago. 

You can't make a dime for many years due to the small fee's generated.That's why you will find many PM's running a shady operation and trying to optimize via other means like offering rehabs, realtor services, etc...I call this the "jack of all trades and master of none".But I get it, folks gotta eat so as long as they stay honest, it's ok.We aren't perfect and make mistakes but those mistakes are honest ones.Thanks again