For many investors who own multiple properties the depreciation of one can be used to offset the income from the other properties as well.

When you are calling for a property manager be sure you are interviewing them!

If I decide to do this, I'll interview several brokerages to find the best fit. 

We went ahead with the purchase and couple of weeks later found out that there were multiple people on the title.

If multiple neighbors detected the same thing about these people, how did my property manager miss it and hand them an application in the first place?

If the mortgage is secured by a second home or an investment property, the multiple financed properties policy applies.

I leverage time/supplies when building multiple at the same time. 

Jim Ostler We are currently developing our portfolio in the Chicagoland area, as previous responses have said finding owners isn’t the easiest task but most owners who are up for this allow you to do this with multiple properties.

The App 'Thumbtack' can be a great resource to see multiple bids and connect with a few contractor's around your area

The secondary goal is to have a cash flowing property.You have multiple problems with your analysis.