If your properties are generating solid cash flow or have appreciated significantly, you might be following a “smart leverage” strategy, à la Grant Cardone.

I personally find that half the battle is just getting myself to write down & track progress

I personally think this is the direction booking sites need to go.

I always recommend starting with a prequalification letter to get a solid view of your purchasing power before heading out into the real estate market.

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. 

The DIYers are welcome, but these kind of deals take a solid 150-200 hrs for the average first timer from start to finish and a minimum cash position of $175k (if you DIY the design/furnishing; more if you want to be hands off).  

Obviously tough to give advice based on minimal info and no info on your personal situation.

Little did I know it would take decades to ripen :)3. bought a foreclosure sale .. traded the house for the 3 acres the person who owned the house. 

The property is insured on your behalf, personally. 

If a person has to ask, at all, I STRONGLY advise to use a PM service for tenant placement.