Very informative nuggets that I can use and take into consideration. 

Take into consideration how old your roof and HVAC are as you may have to replace those later down the road.  

Now, if it was a scenario where you couldn’t rent it out unless you did the upgrades, or the upgrades could be done considerably cheaper, that might change my answer.

The Option Consideration is the cost of that agreement, and in NO WAY is, or should be used as part of the down payment to purchase the property...and is not refundable. 

You pose an interesting consideration, at what point is just getting into a deal a worth while action even though it has impaired performance vs sitting the sidelines and perpetually waiting.

I am only into year 3 of the home and a considerable amount is still going to interest rather than principal.

Thank you David, I will take that into consideration as well.

You may find someone who will do it, but it may be considerably more difficult than if the numbers were flipped.

An additional consideration is that you've also got depreciation recapture on the investment portion and that too will be deferred in the 1031.Getting half the gain tax free gets you out of harms way a little bit. 

We both have good jobs with considerable pay for our area, we make roughly $100K - $110k anally (pretax).