We have local competitors that play the game of low monthly management costs, but gouge for maintenance to make it back.

Play the victim, and see if they will be favorable toward you.

Most professional landlords and property managers don't play the cash for keys game and that is for a good reason.I also agree with Mindy that rewarding bad behavior is a not a good idea.

I see investors betting on appreciation in markets like Austin and Denver getting a hit, I always encourage to play the rent game more and the appreciation less

It’s an expensive route but because I do think she’s going to play the retaliation/discrimination card it’s much better to go strictly by the book here. 

He’ll play the victim in court and drag this out nicely, and/or try and reset the clock with you somehow.

I suppose trying to play the nice guy isn't the best approach here.

If your first friendly reminder did not work then sending a second friendly reminder will likely be received with their second silent "sc**w you".Friendly reminders rarely get results, unfortunately you have to 'play the game" but ultimately you must be very strict, clearly define your requirements and the consequences of not complied.

You really have to play the market's game and list 20-30% below what you think the fair value of the property is. 

I think PayPal is more willing to play the bank, and will decide who is right or wrong, often siding with the buyer.