Not sure my company is going to help you much Jasen, as I'm in the UK.... I have been through several insurers in the last fifteen years, and not one has yet had any issue with it whatsoever. Perhaps it's a problem that's specific to the US market, but I'd find that unlikely.
Remember, you're not insuring the dongle, you're insuring the product licence held within.
Customer - "Hello Mr Insurer, I'd like to insure my copy of Nuendo for £1,500 and my VSL Libraries for £12,000 please"
Insurer - "Hello, that'll be £500"
Customer - "Thankyou"
Edited to add - Hiscox / Hencilla Canworth / Doodson / Palladium etc....