Chicago cap rates are lower then interest rates so what I see clients do is rehab to add a ton of equity/boost rents and then either just hold it or do a partial cash out to get back 1/3 or 1/2 the money in the deal which gives you a higher COC.

Selling one of the properties is not an option because they were both purchased via 1031 funds from dramatically appreciated assets creating a cost basis of next to nothing on these. 

An experienced team or partner can also help boost confidence.Providing a combination of a solid commitment letter, proof of funds, and a clear, professional approach signals you’re serious and capable of closing the deal.

Given your limited cash and high DTI, refinancing after boosting rents might balance risk and reward best.

I could not myself perform the technical labor as I lack the know how, but what I could do was help boost moral.

Post it on fb marketplace and boost the ad and I am sure you will get a million messages but don't make your ad sound like a motivated seller.

Now that rates have doubled, a bank could call notes due, take the property back at a dramatically increased value, and resell it at 8% to make a huge profit.Pace talks about SubTo insurance to protect the investor from these scenarios.

I expect we'll see that change dramatically by June 2025. 

These upgrades revitalized the home, boosting its curb appeal and market value.

Great stuff - this type of regulation is somewhat counter-intuitively a lot better for investors than currently less regulated markets (where you don't know what could change dramatically in the future).