However, I'd really like to get into the nitty gritty numbers, statistics, and marketplace trends as I'm a bit of an analytics guy.

So when this property inevitably gets foreclosed on due to back taxes, he won't care what it does to his credit.However can this property being foreclosed on, can this have any affect on my credit score at all?

I always notice what plants look like they are thriving despite any evidence of care.  

The credit bureaus don't care how much you make, they want to see how well you manage it. 

-What is the best system to be best prepared come tax season as far as having everything organized for my CPA and having the documentation I need in case of an audit?

Look at the threshold carefully.

Do they care about various situations (family with kids, etc)? 

Maybe if you have off the charts risk tolerance...... but someone wanting to retire probably A) doesn't want to deal w/ master lease and B) doesn't care to learn about the benefit of a master lease.Even if avg price was 50k, how many people w/ almost 2mil cash for the down payment or who can qualify for 7+ mil loan are going to want to invest in Mesquite, TX (which has less than 200k people)....

I would take careful notes of how the story changed and send a formal demand for the return of your security deposit - I'd fight it for justice, but there isn't shame in backing away (and not giving them any more money) if you're not up to the fight.

Due to the our health care system unpaId medical bIlls are not unusual.Perhaps the property could be marketed more aggressively to attract more renters?