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.   

Would like advice on markets to focus on - my key hypothesis is to focus on markets with decent employment rates, growing population and presence of contemporary industries such as tech, healthcare, finance, etc and not relying on manufacturing/agriculture.

The repair when properly diagnosed required no parts.

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

But they provide standard documents for all businesses, whether you are a florist, a manufacturer, or a real estate holding company.

(Turns out that work he had done wasn't up to code anyway but I'm so very thankful he didn't destroy anything else.)So, here I am now, it will be about another 2 weeks of sunk costs and time, properly vetting highly recommended contractors with long work histories to obtain updated numbers and a timeline for the work.