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.

Lifestyle-wise we are not interested in house-hacking, but with the right multifamily unit we could owner occupy and be happy.

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

My goal is to supplement my income sufficiently that I no longer have to work OT shifts and can enjoy a comfortable life style with my wife while living in Southern California.My interests in real estate are rental properties for both long term holding and short term rentals, multi-families, and flips.

The repair when properly diagnosed required no parts.

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

(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.