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.

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

I recently started in South Bend and believe you are in a good market.

Ideally, I would like advice from an investor from Bend, OR.

In Bend OR, I know many builders that are pulling maybe 20k profit on 500,000 houses because the price point is so high now that buyers are balking but subs are so busy that they are pricing the GC out of profit.  

Be nice and treat people well even when they're giving their sob story but some will test you early on to see how fast you cave in or are willing to bend the rules a bit.