This property is already contributing to my portfolio’s performance and has strong potential for even greater returns after the planned upgrades are completed.

By self-managing I know which of my properties are problem children and which are my star performers.

So the question for her to decide is do I want to continue investing my retirement in wall street or do I want to move some/all the funds into alternative assets like real estate that can far out perform the stock market.   

Use 20% to calculate individual performance  

The wholesaler also has an obligation to perform, not just you.....

What incentive is there for them to perform well on the deal if they have already made 18k off of you and it is only your money at play. 

The costs could be justified if the rental performs well (a little less profit short term, for longer term appreciation gains and with little to no effort on my part).

I need the asset to perform 365 days of the year, so I am exploring medium term- 1 month medium stays.

I' had confidence in my ability to perform.the seller needs Confidence in Your performance to reduce their risk. 

You likely see no 1500 SF 2 bed + home office's renting for $2,850+ either but that is my best performing unit type.