He had a strong portfolio with solid cash flow, but the big banks just couldn't see past their standard debt to income calculations.What finally worked for him was connecting with a local community bank that actually took the time to understand his overall financial health.

Hey @David Cherkowsky my wife and I house-hacked just outside Alexandria (in the Fairfax County side) and now are in City of Alexandria in the West End.We went the walkout basement route but have friends who did rent by the room (they're past clients of @Russell Brazil). 

However each home and scenario is case by case and must be analyzed.There are also particular property managers to avoid based on many clients' experiences the past few years.

I say biased, because it seems fair and unbiased reporting is a thing of the past.  

Just a headache and full gut imo UNLESS someone already did a full gut rehab within the past 20 years or so4.

@Luke Rusten have personally used a higher price to get sellers to accept my seller financing proposals many times in the past!

It sounds like you are just getting started on your RE journey so I'll point you in a few directions and give you some ideas and some things to think about.Firstly, I'd recommend reading all the books on RE - preferably the ones written more recently as the market has changed drastically over the past few years.

Chicago obviously a bit slower in the winter....this past winter was the slowest it's ever been for us. 

Prices have increased significantly in my market in the past 18 months with savvy sellers now expecting top dollar for their terribly maintained properties.

Because rents lag behind prices, current rents reflect lower prices from the past.