Personally, I do not like any strategy or approach that aims to benefit from the misfortune of others.

I think it is different if you live there, speak the language, know the market.  

Could you pl explain a bit what are the flaws in my approach.

That is a successful approach.  

I'm a guy approaching middle-age, living in Chicago.

This approach balances guest convenience with managing costs and inventory.Happy to connect and share more tips!

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

There are many markets that fit this description.

I would suggest approaching the borrower on an accelerated pay out with an incentive.

Market being hot helped and no permits to deal.