I have other money that'll cost me 10%.

Some may have very small thresholds for repair holdbacks on purchases but this is typically limited to make ready items not to exceed $2,500 in costs to cure.

Assuming your debt is SUPER cheap and only costs you 12% you’ll save $22,800 TAX FREE  So the combination is saving $60k at 12% (or more) is $7,200/yr and $130k in the bank at only 4.5% is another $5,850/yr  so you’re over $13k GUARANTEED instead of a chance to make $7,200 before taxes  

Streamlining Renovations for Efficiency & Cost ControlManaging multiple renovation projects at once demands an operational efficiency that can be tough to achieve.

Creative Freedom: You get to design and transform spaces, which can be personally fulfilling.The Bad: Where Flippers Lose Money⚠️ Underestimating Repair Costs: Surprise structural issues, contractor delays, and material price spikes can kill your budget.⚠️ Market Changes: A hot market today might cool down before you sell, which reduces the profit.⚠️ Financing Challenges: Hard money loans carry high interest rates that nibble into the bottom line.Unrealistic timelines: If you think you're going to be in and out in 60 days, you're sadly mistaken-most flips take longer than expected.Real Talk: Is Fix and Flip Still Worth It?

Evaluate Property ConditionOlder Chicago buildings often have charm—but may come with hidden costs.

Basically dollar cost averaging. 

I'm getting nervous that the area is eventually going to become unlivable because of the prohibitive cost of the insurance.

It sounds like you would make them available at an additional cost?

Even if they don't realize how much money you're costing them now, someone will tell them eventually and I don't think your canned wholesaling response is going to do much to repair the damage.