Your basically asking me to write you a course on how to run your entire business...

Does anyone know if an insurance company that would write a policy in such a circumstance?

Nate,I would suggest finding an independent agent that writes Commercial Insurance.  

Florida has very high insurance premiums and some insurance colonies have stopped writing policies in Florida. 

Get the analysis in writing - if it’s still wrong send them what’s called a QWR requesting a full breakdown and analysis of the escrow payment

Insurance & Roofing industries)  BUT now, one of the Brokers we chat with, say that many of the companies they deal with, are now saying they're not writing policies for roofs older than 8yrs old! 

I would even write it very explicitly :People are tired of very-progressive left wing government policy that removing property rights , creating criminals, protecting criminals , destroying generation and coddling criminals ( in the name of human right or DEI or whatever).Agree @Bruce Woodruff?

My idea for an alternative is to use Bill Pay and just register the CC payment by transferring from the checking account and writing a "check" from the CC account for all the bills paid in that period.  

So get a notebook and write down your goals for real estate for 2024.

And those that still write policies, have raised the rates a LOT.