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.  

I wouldn’t know first hand since I am mainly doing rehabs.

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.

That was the plan, so with expected rent increases and a possible increase in expenses that I don't know about yet, an offer price above asking at maybe around 100k, I shouldn't have a problem achieving my desired 10-11 cap rate. 

Once you find an agent that knows the area and understand what you are looking to achieve, this becomes a beautiful match. 

I agree with everyone else here who highlighted the importance of staying on top of maintenance in old buildings, we achieve regular inspections through filter changes and CO2/smoke detector battery changes.

Best thing to do - make an appointment at Boston P+Z, sit down with a Planner for guidance and educating yourself first hand.