Even if the numbers work for you as is, I'm sure you don't want to overpay and make a loss on the back end.

Selling price on one similar piece of land I found just down the street (but not across from the airstrip) is $50k per Realtor.com - it seems like a loss, even if they demanded a premium on being across from the airstrip.

People were buying houses despite the negative cashflow betting that they'd sell eventually and make a ton of money on the appreciation regardless of the short term cash loss.  

I think i just take the pro-rated 8 months of depreciation in 2016 (for both actually) but when using one of the automated web services to do my taxes, i get a warning talking about net gain or loss Form 8829 , referring me to 8549, and form 4797.  

(Job loss, transfer, medical problems, etc)2.

My rental market is very good and there is no loss for tenants.    

Their loss is not your liability. 

With 20/20 hindsight regulators and plaintiff's attorneys paint targets on these individuals through rescission rights or other legal techniques-They train sponsors to source money through other active investors which inevitably leads to squabbling and a loss of control.  

Is this feasible?

If the out going tenant puts multiple holes into the walls and therefore makes the property un-rent-able  until the holes are fixed, is the out going tenant responsible for the loss in rent income ( 1 month) and can it be deducted from the Damage deposit.