My initial gut feeling is to get the vehicle paid off asap to have extra monthly cash flow to contribute to future reserves for REI.

When we initially fund the company, do we deposit into the Holding LLC? 

If so, then you are off to a good start, but why are you rushing to get limited door income while maxing out your initial debt capability?

The original goal was to rehab, appraise, and replace the private lender with a conventional loan.If I were to sell, I could initially offer 100% O.F. for about 6 months, then I would need to get enough cash (call that amount 150K) out to pay back my private lender. 

Then use those proceeds to buy the new property for cash (and perhaps, down the line, do a cash-out refi on that one, too)Refi isn't going to be quite as good as initially buying with a conventional loan, but is probably still the least expensive way to go.  

I intend to initially focus on single family and duplex properties that require moderate fixes.

It may be better to initially joint-venture with a partner or two, where you all bring capital, and you all are active.

I was unable to sell the property for the listed amount initially of 135k.

For what it's worth, I started out at age 22, the house was kind of dumpy so I did some initial, minimal cosmetic fixes and got a couple of roommates while I lived in the basement, which was not finished and served as a pretty powerful motivator to get it finished in my spare time.

The property cash flows really well for us but it is frustrating that our tenant is causing increased wear and tear on the property and breaking all the rules we initially set in the lease.....