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.  

She could get fussy on who she wants to deal with and could be in a market where there are multiple offers and plenty of investors with cash. 

Investment real estate is not the same as run of the mill residential and most high performing (or otherwise) residential realtors can't see houses from that perspective.

I've pulled multiple absentee owner lists and I always end up mailing someone who has built up a portfolio over the years, but now I want to build a list that specifically targets these people.