So, there is my bet and this session of "Mystery Mortgage Theater" has concluded.

I can’t conclude if his ownership of these properties has been a net positive or a detriment to the community and the schools.Let’s say he loses it all and it all goes up for auction.

I have a similar concern, however I concluded I it doesn't matters too much.

In subsequent calls and emails, I stated that if there was a reason he was not showing the house or accepting a contract, I asked that he just give us a quick call to let us know.What's really confusing is that his "about me" page concludes with: "(name) looks to build lasting business relationships with his clients and always represents their best interest.

You've already concluded that you don't need to use your own money. 

If for any reason they do not get to conclude the investigation they rule in favor of the tenant .

I read a study in which they concluded that Zestimates can be up to 40% off (up or down). 

Which concludes to less income.

Thanks @Andrew Halbert, but I read recently that the best deals through MLS are rare since they'd either been on the market for awhile or the many investors who looked at the property while off market concluded that it wasn't a good deal. 

However, the seller agent told us that the seller had to file chapter 7,  and the process was just concluded yesterday.