Unless there is some reason that a second position could force a sale in inopportune markets, wherein position #1 could suffer a loss, I really don't see why this would be an issue. 

Can you afford to inject large amounts of capitol when required and sustain the property during extended vacancies.Worse case scenario are you cash heavy enough to carry while waiting for a end point to decide to sell.

The house did suffer some water damage during the recent Houston floods.

I don't want to extend this drama any further and complicate things as I will lose valuable summer time in showing the property to potential tenants. 

They are also extending Apollo Beach Blvd thru to Waterset subdivision and eventually to 301.

The 2nd reason it is important to select a short sale experienced Agent is that the Seller can accept your offer just to extend their free stay at their home, without regard to your time and efforts.  

I think we were suffering a little bit from "analysis paralysis", but we will find another one I'm sure!

You're not talking about a career in the arts here, where you need to suffer in order to create.  

He extended the closing twice asking us for more and more in reserves and to complete classes and provide documents.

Did you guys get this house at the price you wanted or did you have to extend yourselves to meet the reserve?