As the great Michael Scott would say: win, win, win. 

It's bad because you'll basically have to compete on price to win.

I occasionally get someone that says, "I know this one guy..." but they can't provide actual details and it's probably just a rumor.Almost all legal disputes are over security deposits and very small amounts.Large suits involve injuries, which are only a risk if the landlord is negligent (e.g. fails to repair a broken step and the tenant falls).Even if the landlord is guilty, the suit will most likely be settled out of court and covered by insurance.Even if it goes to court, insurance will cover the costs.The odds of a landlord losing a lawsuit for more money than the average insurance policy will pay are about the same as winning the lottery or being struck by lightning twice.

It sounds like he has assets that you could go after if he doesn't pay any judgement you win. 

Even if you win, you'll lose in the end.If you feel the prices are out of line, ask for more quotes.

There's a few other things to think about too: 1 - Possible owner financing if he wants to still get a stream of income into retirement at an attractive rate compared to the rest of the market (win/win scenario, you don't need to come up with as much cash, and he makes a little $ on the %) 2 - Consider a post possession if he needs some time to move out but needs the cash up front for whatever reason 3 - Leave all the furniture/junk in the property and you'll handle clean up etc. 

But it doesn’t take many properties to turn many disappointments into a massive win. 

If you do everything right, there is way less chance for her to win against you.

If you are going at this thinking you are going in bidding and winning above it, you are going to be disappointed.Another Question:Do you think interest rates trending or heading back down is good or bad for non performing note investors?

Winning bid gets the property, the quiet title order and the clerk's deed.