I want a real estate agent with a hustler's mentality, who knows the neighborhoods, studies appreciation and deal analysis already, understands short-term rentals, and is potentially looking to be a scalable partner with me.

The only place this would appear to make sense is in Class D neighborhoods which could cash flow.You have rights to income but nothing else - sounds like an unsecured note at the end of the day.Chris you make good points.  

Also, neighborhoods matter.

Chicago has plenty of opportunities for value-add projects, and I'd be happy to share some insights or introduce you to a few local investors I've worked with.Feel free to reach out if you want to talk strategy or specific neighborhoods!

For the most part vs focusing on a specific neighborhood or two I would say keep you options open to all. 

I own in the Avenue neighborhood and feel it has the has the strongest prospect for growth. 

I am hoping to make connections to learn more about this market, which neighborhoods to focus on, as well as learn some pro tips as I begin my investing journey.To note, I have begun the loan pre-approval process and have a dedicated agent that is eager to find me a great property. 

I live here in Columbus, and it's very attainable to house hack a duplex for $400,000-$600,000 in an A-class neighborhood and gross $3,500-$5,000 in rent, which is why I asked.  

Let's assume that the neighborhood is a C class and the median income of the city is greater than 3X of the market rent.Here are some of the considerations I've come up with so far:- Units are in need of renovation and capex is too high or not available- Unit quality is not the same as market - Seller is worried about losing tenants due to increase- Vacancy rates are high or filling units have been difficult- Rent increase would take multiple increases over multiple lease periods to get to market rate if seller is trying to retain the same tenant- Seller inherited property and just want to liquidate- Seller needs to liquidate quickly (financial burden, sickness, quick exit from land-lording)It seems like I might be missing a warning sign about a deal if they are selling with current rents that are under market; but again, this seems to be most of the properties I've underwritten.And in the same vein, what should I be worried about when purchasing a deal with under market rent with the intention of raising them after purchase. 

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.