My current homeowners insurance policy is under one address, but covers both sides of the duplex.

With the home being "underwater" in both respects, why would a homeowner want to make their mortgage payment if they can't get their insurer to cover the repairs.

Hire a PM and have them evaluate what rent should be, the PM i use covers your area and is managing 400+/- units all over northern and NE WI

@Mark SpritzSee IRS Publication 560 for more information on the self-employment income rules as it covers those rules pretty well.

I've given people I know who trust me personal guarantees and got loans for 1/2 my downpayment (they know I'm good for it as I can cover the debt on a global cash flow level).

The income and LTV can cover another 2nd loan as well. 

One thing that was appealing to me was that there was a section 8 tenant in there and the rent was high enough to cover the mortgage and HOAs and then some.

Since there are no bites on the MLS and not enough room for an investor to make a profit, I only see 2 options.Sell for less than you owe and bring cash to closing to cover the difference.Go through foreclosure.Sorry this deal went sideways on you.

I thought about having a property management company manage the property but I do believe this is something I could do on my own and utilize on line screening services as well as checking local evictions public records. 

That hardly covers anything unless it's just been fully renovated