Then hire one that sounds competent and that you can get along with.

Another thought - are you considering an FHA loan on the next one?

I am active duty military and plan to use the property for deployments/holidays for my family to stay near relatives until I separate in 4 years, then to use that property as one of several future investment properties.

I've been knocking on doors, there is one that seems like it's abandoned, however despite finding the owners name from tax records I cannot seem to get in contract with them to make an offer (despite trying x, y and z). 

Charleston (in my biased opinion) is one the best places to live in the country.

Yeah, I saw that dozer video too, that's a big one!

I only spoke with one person so far and they scheduled for more information gathering/ rental investment calls from them this upcoming week.

I had a similar idea (having one of the mortgage brokers I know underwrite any prospective buyers.

I'd bring island out a little more. my advice is make sure all rooms are 110 sq ft minimum. some of these look super small. we build a very similar one in our market.

The loan is with you, not with your tenant, so none of that means anything to them - in fact because you live in one unit and it's under 4, if you were self-managing you don't even have to abide by fair housing laws (at least on the federal level).