I just had a 20 minute phone call with a wonderful lady at Hagerty. She got into the detail of this with me, and explained some of why there might be different answers given to different people.
They apparently get a ton of crazy inquiries from people who are just trying to get lower car insurance rates, and the customer service reps are being challenged by people with the weirdest scenarios all the time. She said she literally got a call from a guy who wanted "collector car insurance" on his 1970s pickup truck and asked her if it would be covered when he was using it to make his twice-weekly trip to the dump to unload a full bed of scrap metal and garbage. Turns out it's an old rough pickup truck, isn't actually a collector car at all, and he was just trying to save $100 a year compared to his normal policy.
I think they've gotten to a point where they just assume that if someone is asking a bunch of scenario questions about what's covered, that they're probably going to be doing wrong things with the car and are asking a bunch of questions to try to game the system, and it's better to just avoid the risks. She said the chat is the absolute worst for this, and wasn't surprised that KAR120C got a dismissive answer. She understood where we were coming from though, and wanted to clarify some things.
What she told me regarding the stated scenario, which is a pleasure trip to the mountains with my spouse to stay at a hotel and then return, is that if there's a claim that arises from damage in the parking lot of a hotel, the claims adjuster is going to ask some pointed questions about why the car was in the parking lot of a hotel. If it turns out that you were genuinely taking a pleasure trip and there was some unfortunate loss, then it's covered. If it turns out to have been something else, like you were actually traveling for work, or you're secretly an employee of the hotel, or you actually rented the car out on Turo and someone abandoned it at a hotel... in all those cases you aren't going to be covered. Apparently they've been burned
a lot on stuff like this, because so many people are entitled assholes (my words, not hers).
They do have additional coverages that can be added to the policy that are oriented toward people who travel with the car on a regular basis. These are NOT required coverages to use the car for travel, but they do add additional benefits that can come in handy if a trip gets interrupted. Those are called 1. Motorsports Advantage and 2. Traveling Collector. The first is designed for folks who travel to attend major motorsports events and might have scenarios arise that they'd like covered, like the use of a golf cart or trip interruption coverages. This cost $20 extra per year, and I added it. The second (Traveling Collector) is for folks who regularly attend large car shows and travel long distances to do so, and adds coverage for things like memorabilia that are often part of that "show and display" pattern of use. That costs $25 extra per year, but doesn't match my pattern of use so I didn't add it.
More detail on available optional coverages:
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Hope this helps others! I found it useful info.
Thanks,
Porter