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?

Anything 1m+ will be harder to sell (I am making assumptions on the price), there is simply a smaller pool of buyers.

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?

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

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. 

The term curb appeal is simply referring to the home's exterior being appealing, which doesn't have anything to do with plants or pots or items directly.

I don't think that simply having an LLC would protect you from that Bubba the roofer.

The seller not necessarily settled, Seller simply took the only offer they had.