I'd also verify that with a final walk-through a couple of hours before closing.I'm assuming that there is no such clause in the P&S, but if there is, I think you can sue for specific performance/breach of contract.Not to rub salt in the wound, but this is a perfect example of where a good buyer's agent is worth his weight in gold.  

I'm surprised by the overall lack of awareness that many Realtors in my market seem to have in the power of an escalation clause used properly.

You cannot STR on 99% of the condos / complexes in PS proper, close to the main drag.

You certainly need to speak with a lender and go through these scenarios so they can advise you properly.  

I see that more on the East coast as older cities like Richmond have gentrified, and correct me if I'm wrong but I'd guess that the properties are still on the older side even though they are in good areas.That's true, a lot of Richmond City proper is older buildings.

As for the deck that is a bit harder to screw up as long as it is sealed properly the rest is just you inspecting upon completion of work, as always get someone licensed and bonded.

Beach is a whole different thing, and ultimately my post (see title) was looking for direction on the proper place to post my questions or even find a specific person to help me evaluate the opportunity (maybe a pro or co-host opportunity) because I learned in two minutes on this forum since I joined that there is more to it than the “profit” from one year of STR.

Both of those strategies if done properly will help you implement your plan of obtaining 3-4 more properties.   

The repair when properly diagnosed required no parts.

We aren't talking about a caring landlord here who does proper maintenance.