They simply do Fannie, Freddie, FHA, VA, and USDA loans.

I love how you emphasized the importance of educating investors about the market cycle and long-term strategies—it’s all about creating a win-win partnership. 

The chance of winning is slim to nil.

Throw in that you can dramatically increase the value of the property once you show consistent rent rolls much higher than when the space was used for LTR, and you have a big win. 

May this year bring you strategic wins and profitable ventures in an evolving market landscape.

I'm not saying this will never happen to me, but I'd probably be vastly more likely to win the lottery before that happened haha.I can attest to #8 as well.

Does that sound like a winning strategy to you?

Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?

In my experience, it is worth simply reaching out to your realtor first. 

Even if you are not cash flowing on day one, that's okay (in my opinion), you're not paying the full mortgage on your own, which in of itself is a huge win and you learn other tangible real estate investing skills along the way by simply owning.