I essentially reverse-engineered all of this and came back to the amounts I should then be contributing to my retirement accounts and the down payment savings account each pay period.  

I hesitate doing a short sale as I have excellent credit and would like to use that to my advantage as an investor, so I’ve essentially felt stuck in this condo for almost 10 years now.

I though it was a pay a fee done paperwork?

@Dustin CavalierRisk, albeit mitigated risk, is an essential part of being a successful entrepreneur so with little time, little money and a disdain for risk, you will have a long row to hoe.  

I have a property in DC where the roof is essentially flat and you could never see solar panels on the roof.

Also finding a GREAT contract attorney that can protect all parties, including you the agent.Protecting TBer - use a payment servicing center to take rent and pay PITI; record a memorandum of agreement; create all paperwork for sale in the future to be held in escrow until the property transaction is concluded; allowing extensions if TBer needs more time to get a mortgage.Protecting Seller - strong paperwork in case of default by TBer, being fair to TBer as to sales price in case the property does not appraise in the future, making sure the option money is non refundable.More info here

Essentially acting like a middleman...

I don't mind paying essentially the mortgage note and having my expenses covered seeing as this is financially better than renting.

Essentially, our long term goal is to pool together some money, and buy a few properties. 

Walked through my valuation of the property with my agent who sent over the paperwork and reviewed with the listing agent.