The length of time owning the home, along with the hours invested, which caused me to miss time on other properties makes me feel like this is actually a loss.

I'm definitely open to all other advice as well, but am concerned about buying a property where I think I can rent out the MIL, but then hit some law that prevents me from doing so, or causes expensive alteration to meet MIL regulations.Thanks!

Also, people will move in with family or friends causing more units to become available.

Just saying it was rented already will likely cause issues when they see it still listed days later.

This is causing it to miss the property expenses for those columns. 

It never occurred to me that the land contract would cause any hang-ups in the refi process and we made it all the way to a week out from closing before it came up.  

@Robert Courtney From my experience, inherited tenants have caused 100% of any issues that I've had so far and I've realized that the sooner you can get your own, well screened tenants in the better.

Any idea what about a 506(b) would cause this divergence in execution?

From the many posts I have read the basic Cash Flow problems are caused by the low down payment.

If you file, your filing for Cause,, Failure to vacate after proper notice of non-renewal.