Is it unusual to ask to speak with a current tenant living there?

That's unusual for someone your age.

So if A ends up showing income of $10,000And B ends up with a loss on paper after of $4,000You pay tax on $6,000.

I have a buy-and-hold portfolio consisting of SFRs and small multifamilies in South Bend and Chicagoland, and would like to buy something larger (5+ units) in North Indiana/Southern Michigan.

There's simply too much corporate greed - they will absolutely bend the rules for profit - guaranteed. 

Circumstance dependent.Before this becomes a little to much of a mind bend.  

We are highly interested in the river bend area as well.

Your sphere unless unusually large will get you a few deals in a year.

My target markets are Bend, Oregon or Portland, Oregon (my home town). 

These prices are not fixed, we occasionally find class A properties for $175,000 but that is unusual.