Just shop around online, look for properties similar to yours, add them to favorites and watch them to see how long it takes for them to rent.

Take your $5k of saving, and borrow another 5K by placing a home equity line of credit on your house.  

Solid area, home just went on the market.

That’s fine down the line, but for your first property, I’d lean toward familiarity.2.

Than I thought it was all the things that could go wrong in the flip, hidden gems like K&T hidden in the walls, shot main-lines, etc.....   

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

Some lenders work with 220+ lenders and can really understand which lenders are best for you based on your situation. 

I would only underwrite based on actual rents not proforma.

While @Phillip Austin mentioned Raleigh is a higher returns its just very much a appreciation market, you will not find rentals that cashflow, so depending on your goals its a good or bad market.

My advice when you're checking out an investment property, don't get too hung up on property taxes.