However, if you don't ever put your foot down tenants tend to keep pushing farther and farther testing your limits and before you know it you could be having rent come in at the end of the month instead of the beginning as they know there are no real consequences.

There’s nothing you can do to prevent a mentally compromised person from behaving mentally compromised in your property.

I also mentioned to him that I might be having a big job coming in for him in the future and he said he will get insured.

Having "nuttin' ta lose" makes a borrower behave differently from one who is fighting to keeps what is his.2.

Sam, you are thinking and behaving like the realtor.

If you enjoy what you're doing, then you must be having fun.

Help them out with other non-real estate related problems they may be having.

I think it is a situation where people are so influenced by propaganda ,even at the highest levels of local government ( Mayor,etc) that they behave in an irrational way.Have you considered other local markets where the cities might be possibly be less hostile towards investors...

Anyways I was going to just start the process now and was planning to see how market behaves to buy it in 6 months or so.  

We have well behaved tenants because M2M lets us be in control.