Last thing you want is someone with a gambling problem that bets your operating account on black.Have regular conversations.

I get to purchase another property, my investor is thrilled at their bonus, and my cashflow through property management increases!

I get most of my thrill out of cheap hobbies...

It was a bit of a gamble up front because I paid for it myself entirely while pretty much all of my classmates had tuition reimbursement through their employers (for instance, a few of my classmates worked for Disney,  who pay their full-time employees 75% of their education costs.

Only "out" I see is if you can document his "peeping behavior" on video....then it becomes a police matter, restraining orders and legal grounds to evict him.Otherwise you have to hope he violates something else on lease....My gut feeling is the "cash for keys" is a very iffy offer for a creepy guy like this...... most of them seem to relish the fact that they are creeping you out, so it will add to the thrill for them.

How many investors out there have let fear of losing money, stop them from taking a gamble on a property?

There is always an opportunity cost with waiting or trying to gamble. 

This woman was thrilled to have the potential problem house off her hands, and I bought a great house for a few hundred dollars of moving money. 

Youd see the guy out and about, and he was just a free man running all the drugs and gambling in town.

In many cases these investors put almost all or a considerable part of their net worth buying these type of properties and that can be in many cases nothing more than gambling.