I've thought of having some sort of 6 month challenge where a reward would be given if no payments are missed but that may become a pain to deal with and I have a hard time justifying why I have to lose money in order to collect the agreed to rent.

I have a pretty good job, but every day I'm painfully aware of the the pace we have to operate at with our daily schedule.  

If you do sell consider lease option as you can usually ask a higher price for the property and take some of the pain out of selling for a loss.  

@Brandon Turner This would be a great topic for a podcast as it is a pain point for many newbies and veteran investors.

IMO it can be an extra pain when you attempt to do a cash out refinance.

Aren't we all.But recently, the pain / pleasure drive made it clear to me that I do have a why.  

When I'm focusing on creative something, before jumping into building it I always ask for the "Pain" so I can build the solution.What I do is send out an email to my hundred of real estate, and get their feedback on what they're struggling whith.

We've missed opportunities too when we didn't have things in order.These are painful moments.

I've inherited a few rentals with chronic late payers.

It would be interesting to know if oil was to stay under $50/barrel for a prolonged period of time, if there would be additional layoffs in the sector or if most of that pain is behind us.