Eliminate debt, establish a budget, and save.

I purchase my personal investments to maximize their equity and hold long term.

Due to the current interest rates, you probably can't live for free, but you can definitely learn how to house hack in that first year, reduced your personal housing costs, learn the rent by room/co-living strategy on-site, and then probably break-even after move out, but most importantly, it is possible to make that work in 2025 with today's rates.It just takes being open-minded and willing to be flexible for the 1st year.  

I’m not a former IRS person.

I have a situation where a person I know is moving out of the country and would be looking to put their home for sale in the summer.

It's also worth noting that, given my community development background, the intent is to help them refi into traditional financing after they've established a payment history.

I recommend you decide, take action, and move on. 

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

Dumb question - but are these auctions online only, or in-person? 

Personally, I would hang on to the cash.