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?

This is what I am encountering, in the current Mortgage Industry.If you think you will go FHA, Conventional, FHA 203k, etc. and then Quit Claim the property, to a LLC, or a Land Trust you run the risk of the lender discovering a Title Transfer occurred and activating the "Acceleration Clause" or "Due on Sale Clause" that requires the loan to be paid in full, within 'x' number of days.

It may create a problem for you later if your bank discovers the account is owned by an LLC that no longer exists.

I am not a tax professional trying to sell you my services I am simply providing my perspective. 

If I pay it off, I could maximize cash flow earlier, reducing financial stress and allowing me to focus on other ventures or simply enjoy life more.On the other hand, I know some people advocate for keeping cheap debt and using the extra cash to invest elsewhere for potentially higher returns.Why I’m leaning toward paying it off:Security: No debt = peace of mind.Financial freedom earlier: A fully paid-off rental would give me a significant monthly cash flow?

So maybe this simply won't work. 

The way wholesalers get around this is by claiming to simply be marketing the contract and not the property itself (hard to do legally), or by doing a double close (buying the property then reselling it immediately).

DSCR loans underwrite to the income of the property, and do not require your personal income, taxes, debt-to-income ratio, etc.Of the 1,100+ loans that our team closed last year, I want to say that only 1% to 2% of those were closed in a borrower's personal name.So, it is pretty irregular for us to process an investment property loan under a personal name.Clients usually opt for closing in their personal name if they simply do not have an LLC established yet. 

I’ve often seen this happen where initial approval is given, but debt-to-income issues arise once they discover you’re purchasing another property.

If you discovered the issue before paying for the appraisal that could hopefully save some costs (in case the appraiser is with the wrong AMC).Pre-vetting with the lender on rental history/AIRbnb/1007 as well as seasoning could help.