Multiple people including myself have tried to caution him of the the true costs but he's been repeatedly dismissive and has made it clear we give him motivation and he wants to prove us all wrong (whatever that means). 

That was an excellent non-answer to my question, Skyler. hihi :)No they are not all the same. some are only interested in dealing with conventional purchases other are as you say better at handling assignments or double closes, some are commercial specialty, etc....A investor friendly one would be, at least from my point of view, one that understands there may need to be some last minute wheeling, dealing, and adjustment made to close a deal, understand what needs to be done and do not freak out about creative deals.Maybe my understanding or thoughts are wrong but that's what I meant by investor friendlyregards :) 

I can definitely attribute a lot of my success over the last few years due to the connections I made on Bigger Pockets and the things I've just simply learned by listening to and reading all the great info available here!

As a real estate broker I would make the same suggestion but as a buyer I feel so lost..

I made an effort to connect with everyone until I eventually connected with the top investor/broker.

Again, these are made-up examples but when I started, I was looking at one property in Chicago vs THREE in Indiana and the property taxes overall were about 1/4 the cost of Chicago and evictions of 3wks vs 6 months or more in Chicago.

If it's worth it to you now, I'd find a real estate lawyer and ask if they have a simple lease agreement they made.

What made you interested in investing in this type of deal?

@Edward Toomey V I feel like this is a frustration for us all in the property management game.

What made you interested in investing in this type of deal?