While posting adds on Craig's list or other means would seam to be a good option and perhaps get some money out of it, I did not want any more strangers around the property or know it even exists.

We trust our investment to strangers.

I you are going to take on a stranger living in your home be sure of your screening, and don't take anybody's word for anything; check it out yourself.

It's not like they could say "Uh, some stranger came into the house garage and covered it while we were smoking dope."

They don’t do much marketing, it’s up to you to promote it, so you probably won’t have a lot of strangers ask to book.

You can't ask these people to trust a stranger's word of honor, especially a young, admittedly inexperienced stranger who owns the roof over their head.If you don't agree with me, then at least do what @Bryan Balducki says.

This group of owners were pretty well heeled so all was ok according to him.Sounds like something that will require lots of research as you are going into a RE deal with a bunch of strangers where the rules aren't well spelled out.

This strategy would probably work best near a university as college-aged individuals tend to be more accepting of sharing space with strangers, or other spots like Scottsdale or Phoenix.

When you are starting out, you better have a very compelling story to convince complete strangers to invest (very hard, but not impossible).  

Before “applying” and sending him my personal and financial information how can we be careful and make sure we are not sharing those things with a stranger?