@James W.mention didn't work for me....Wasn't implying you're a dummy, congrats on your early success!

Your title implies to me the "system" of rolling over cash out refinancing, in reality that has several barriers and your ability to pay will become a factor as well as the number of loans as well as loan concentrations to one borrower that lenders will be concerned with, this isn't a go on forever strategy. 

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Not to steal Bill's thunder Julian but to address your question we have to pause on the idea that you implied of "perfectly good".  

You said that you a sure that you are capable of doing DIY portions to me this implies that you have experience enough that you can mentor in this area.

Those lots had owners in the past and that implies value. 

It is for the 2 reasons outlined above that I always prefer to have the leases automatically go month-to-month after the initial lease term (this is implied in Connecticut), otherwise as a landlord you sort of paint yourself into a corner. no?

Assignment may be implied by default but I'm assuming adding " and assigns" after the buyer name is sufficient. 

If there are no buyers out there then either the marketing has been bad or the values are lower than the 1 comp implies.

Or the short sale amount plus costs is greater money to the bank compared to an auction and all the costs/delays that implies.