I am counting on that contract/lease to pay my bills, and if you agreed to it for a set amount of time, I am expecting that to be fulfilled. 

With it being April, I figured we may be able to draw out closing to June and then fulfill the "reasonable timeframe" occupancy requirement by September 2015 (one year from the time we bought our current property).Has anyone had a similar experience or have insight in how this deal may go if I apply for a loan?

Legal interest is delivered upon successful contract terms fulfillment.  

One was an average tenant that fulfilled his lease with no problems.  

As with you, my rate of fulfillment is 1 our of 50 or but I'm out there and in front of most other people who don't see a deal until it's too late.

You need to ensure you are generating enough cash flow to service debt, maintain the property and fulfill your duties as landlord, etc.  

Its a good feeling knowing you are fulfilling the full potential of your property.

***now my tenant is paying off the intial 21k mortgage, whilst fulfilling their 31k × 11.2%.

My lawyer said that when doing a double escrow, you don't have to disclose your intent to sell to an end cash-buyer because technically you bought the property and owned it for a minute and therefore fulfilled all the contractual agreements.

The requirements are generally hard wired into the terms and the lender is just fulfilling them in order to get paid.I have never dealt with PMI directly as I avoid them like the plague.