Chicago cap rates are actually much higher then other comparable sized cities.

While shopping for home insurance, I kept receiving higher premium quotes.

If I put myself in the shoes of the outside partner/investor friend, I would be very concerned because: 1) unclear and/or potentially conflicting business plan, 2) even with clarity in the BRRRR business plan, unclear in the viability of pulling it off with these market conditions, 3) the chances of dispute seems very high, especially if you're going to live in. 4 years ago, I went through a  similar thought process when purchasing an investing property with mainly my family money, while considering an outside investor to rehab for higher STR ROI... 

We manage a bunch of ADU’s and higher density new builds for investors in Raleigh and Durham.

Explore multifamily or out-of-state investments for higher yields.Setting up an LLC provides liability protection but has no tax benefit for you now.This post does not create a CPA-Client relationship.

That's pretty much the only way you can consistently get higher than market rent via S8.Also, don't make the mistake of assuming the S8 voucher amount is 100% for rent.

If you are not building in sufficient capex, then these costs could be higher, if not much higher.

But those have higher rates. 

And I think a lot of companies will realize that productivity is generally higher in cooler climates.

From what I’ve heard in a piece by Forbes, focusing on unique features can lead to higher long-term rental satisfaction... especially if your tenants want a few animals or more outdoor space.