My guess is that your property management company approached the homeowner without much empathy, and the occupant is right to be skeptical as many people don't realize they've lost the home.

Basically out of all the people that were interested, I have chosen the people I liked/trusted the most. 

I coach people on how to build private money brokerages and eventually start lending their own money. 

It seems like there's enough people doing both that there should be a good software solution...

What would be nice is also to have someone on more often who has been around a longer period of time (ala pre-2008) as most people in real estate only know the good times and what we have ahead of us is not the good times.

First, check the people.

At the end of the day, it's my opinion that people should invest where they have an edge.

I can reply to topics other people have started but I can figure out how to start my own topic...getting frustrated I've looked all over this page for 10 minutes. 

I'm working on helping some clients/friends of mine get their condo rented as a medium term rental, but not getting many hits on it, only one person that never answered me back after multiple calls and texts (stay has to be 30 days or longer).  

If these people are "professional tenants," there are all kinds of scams that they could be running.