Looking for some guidance: Covering house with two policies

[Digger Odell]

Hello to all. Hope someone with insurance expertise can provide some advice...

I'm closing up my office after 20 years, downsizing my business, and selling my home (in the Spring). I will close on a place soon that was once commercial but converted years ago to residential.  Have already spoken to the zoning office and they are fine with my plans as long as no sign and nothing visible from the street.

So here's the deal. I have a full business insurance policy for both contents (cost to replace) and complete liability plus another for workman's comp for freelancers I may hire on a one days basis. That work being done away from the home.

I still need to purchase a home owners policy. The business policy agent will not combine the two saying I need a separate policy. That's fine I can live with that. My problem has to do with the square footage issue. The town assessor has it as well just south of 4000 square feet but this is incorrect. Livable (heated) space is around 2450 square feet. The rest being unheated storage, garage/workshop, loading dock (yep, that's right) and an open-on-the-end car port. The agents I have contacted say they must take what the town states so the premium is quite high. They are quoting me to insure/replace a house costing close to $400K when I am paying less than half that for the place. Have not even discussed the second policy with them as yet.

The town is undergoing a reevaluation right now, this month and I plan to ask for a hearing on the footage issue as well as the current assessment, which is way high also. Should I wait to insure and take these results back to the agents? That means no home owners insurance coverage for perhaps a month or more? Will this likely change things or will they go back to that old size?

There is also the issue of coverage within the home. I plan to use around 500 square feet for the office about of the 2540 total size. Would each policy be based on their respective sizes or will they likely overlap? 

Appreciate the help on this.