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. 

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

I've got stories that would be hard to believe on some of my seller financing deals, contract on a napkin, personal check for a notarized deed, hand shake deals, etc., etc. and a LOT of fun.

We purchased it off market, as-is, and as it was our personal home, we renovated over time.

You are going to send your wife to personally unclog that toilet.

It’s usually best to open a separate business checking account so your rental income and expenses stay organized and away from personal funds.

I personally would recommend the last method.

@Joe Gellenbeck Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

Hi Srikanth, I’ve been investing in Cleveland neighborhoods with a similar focus, targeting properties that align with appreciation potential while attracting quality tenants.

Welcome to Bigger Pockets @Joshua KeimAs a fellow Memphis native, I’d love the opportunity to connect in person and discuss strategies with you!