Wanted to provide an update:
I decided to go with Hagerty (for this year at least) for a few reasons, even though they were so much more expensive.
Grundy and American Collectors were ADAMANT that any overnight stay in a garage/parking spot/whatever that was NOT my home was not covered. Hagerty agents (and i spoke to 3) were clear that it was covered.
Grundy, even though they state that they want you to "drive the car" were fairly strict about usage. I provided a few scenarios and all were met with "probably not covered."
As @Jon T stated, that "frequently" wording in Hagerty's policy makes all the difference. All of their agents were positive that it meant that I could use the car as wanted, short of making it my daily driver. They were clear that they very rarely ever deny a claim.
My umbrella package insurance agent (2 homes, 5 cars, life, buildings ) was clear that I should go with Hagerty, even at the high price. He has 30 years of history dealing with them and praised their overall coverage and claim handling, even though he has nothing to gain from them and does not deal with them in any way.
They were able to underwrite the policy immediately after i provided pics, VIN, and registration. So I'm covered in preparation of the Monday delivery.
I guess my only question is why my policy differs in price from @Jon T, even though we have exact same parameters.
Hagerty can be cancelled at any time and will prorate the policy time left and cut a check, so I'm not too stressed. I can always change over if I find something better.
Thanks again everyone who chimed in. I'd be lost without you as a resource.