Hey @Max BellinoI'm from Worcester  area as well and have a solid cost segragation guy. i see this is a month old but shoot me a DM if you're still looking

As a CFA you probably know the old quote from Warren Buffett who said something like "buy what you know and understand". 

As an investor in a market where cash flow does not come often and appreciation is a bigger play, I understand your mindset. 

A solid property management team (or maybe multiple PMs if your portfolio is large enough) is a must for out of state investing.

The rapid turnaround exemplifies our ability to execute efficient deals while delivering solid returns for our partners.

It is 100% the buyer's / investor's responsibility to do Solid Due Diligence before purchase. 

., and I still love Cook County because I have a solid team and underwrite deals properly.I think @Paul De Luca nailed it on the head, though - it seems like you are quite risk-adverse, so maybe given your risk tolerance, it's not the best idea, but if it were me, I would not think twice about it, and find a rock start property manager who knows exactly how to vet tenants.

Some buyers enter these agreements without fully understanding the financial commitment, often influenced by overly optimistic advice.

I own several duplexes there and they’ve been solid investments with no issues finding renters.

You'll want to ask about their experience, read reviews, understand their availability, pricing, insurance / bonding, and how they safeguard their funds.