However, our tenant turned out to be problematic—late payments, issues that led to an eviction, and additional repair costs before we could relist the property for sale.Now, after months of making mortgage payments out of pocket, we finally have an offer.

Just say no.I would almost never do this trade unless all my downside, including potential unknowns, were completely compensated for. 

With running this "business" there will be operational input costs.

Additional software estimates renovation costs and provides actionable analytics.

I wondering if I can deduct any of the repair, closing cost and deprecation on taxes. 

.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

I have a pretty large emergency fund in place for those properties, but I wonder if that capital could be better employed elsewhere (potentially acquire another property).  

A second STR in a market with year-round cash flow potential might balance out your portfolio and give you more consistent income.

Heck, you process debit cards if you insist for 1/10th the cost and non-reversible. 

Angel investors might be interested, but you'll likely have to give up a portion of the ownership or future profits, and there could be potential complications in managing the investor's expectations and involvement.