Hello all,I am hoping to get some opinions on optimal wealth management for my long and short term goals.Background: Currently 18yo in college.

That 30 day clock is ticking and you are not achieving anything by holding on to their deposit for the full 30 days.  

A List Broker can offer suggestions to optimize a list for your area, including some of the newer motivated owner occupied segments to mix. in This can be good since as @Brian Midden says, in most markets  Absentee Owners are getting a lot of offers.You might be able to get better pricing than with ListSouce

The reason you’d do this is to optimally protect you from being sued in every direction.If you’re personally sued then some states allow the plaintiff to dig into anything you officially own, entities owned by you, and anything owned by those entities.

I've been managing property for nearly 20 years and my philosophy has always been to work together to achieve the common goal.

And, congratulations on that over-achiever family of yours. 

Once complete switch units and rent the unit with the TLC at market rate.If you get deployed to a different location, rent the unit that you are vacating.I know the cash flow ratio is required for 80% LTV to achieve some cash flow but I do not know what the cash flow ratio needs to be at the high LTV of a VA loan.  

If the tenant and lease terms are acceptable, then financing 60% of appraised value should be achievable, even if that loan amount represents a higher percentage of your cost.

Depending on how quickly you hope to achieve financial independence (FI), leveraging will put you into a position to get there faster. 

The only factor that should matter is which market fits your investment objective best and allows you to achieve those objectives.