My earned commission would wash out most commissions offered on the listing side if I had to go that route. 

It may sound nice to pay a 5% management fee but the extra fees can add up to be more than the other company that charges 10% with no add-on fees.

If you can find someone like that, it is worth paying a bit extra for their expertise.

In the past we have given our private lenders a 1099-Misc to report their earnings with us for the year.

Make sure it’s enough profits to make it worth the extra costs/hassles. 

And I can charge them an extra $50 for the electric and water usage?

My prior experience in real estate investment is that I bought and sold a home, and while living there I rented out the extra rooms.

There are only so many buyers, and crossing state lines to sell carries extra risk.

Then when you move to MA you can purchase your primary residence with the VA loan (ideally a multifamily property) and your extra cash you can use to invest.Best of luck my man and let me know if you have any questions about you VA loan benefits.

We have our loans fully serviced and sometimes I wonder if it's worth the extra money we pay since the servicer's loss mitgation efforts varied from extremely poor to average.