The insurance is for a rental condo property located in Madison, Wisconsin I’m wondering if anyone knows of any other insurance company.

All companies must apply unless you meet a certain exemption.

I'm an investor and property management company owner in central CT. 

It's by a company called Stonefeather Marketing and automates audience building on FB.

Those companies you asked about are more for deal finding and direct contact to off-market sellers, is that what you are looking for? 

There is a "sponsor exemption" but that only allows an unlicensed person to raise money but it cannot be more than 50% of their duties and the pay they receive cannot be based on how much they raised.If you have never raised $, a family office will be off the table as they typically want the company to ahve atleast $50-$100M in assets. 

My insurance company sent guy to inspect once.

I like smaller companies whose owners are not brand new but not old and burned out either.

How does the transaction work between me personally and my holding company LLC?

It may sound nice to pay a 6% management fee but the extra fees can add up to be more than the other company that charges 10% with no additional fees.