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. 

Don't solely rely on third-party management companies; instead, focus on building a solid asset management plan and, if needed, bring in experts or partners who excel in this field.

ThenMailchimp **** me down, and two other email companies rejected my application.  

Consider getting a real estate license and joining a company that focuses on working with investors.

We have hired   a property management company for all three rentals.

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

Other companies people use are SNSC, FCI, Landhome, Homekey and others.That would be your best bet.

C. and @Trevor Laramee I went through a local insurance company and was happy with the rate.

New companies like Intel, Amazon, and Google are also investing here.

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