However, what I would suggest based on your expertise as a contractor is going into a semi-fixer upper and make minor repairs to boost equity as well as savings. 

The current owners are putting the moral dilemma on the new owners and still want full market value.

The fact that they are telling people otherwise is morally questionable for any investor or inner circle wannabe.  

Adding livable space or smart home features can significantly boost home value.

With the new subway line being built nearby, do you think this could boost demand for smaller, ADU-style units?

With $750K, start by focusing on cash-flowing rental properties in stable markets like Indianapolis, Kansas City, or Birmingham, blending appreciation and income.Use financing strategically to scale while preserving liquidity for value-add opportunities like BRRRR or small multifamily properties.Allocate a portion of funds for flips or mobile home parks to diversify and boost capital.

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

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.

Next, I'll be pivoting into subsidized housing investment and collecting rent $ from the government as i truly do believe this is a way to boost CoC return percentages in today's market.

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.