I have all of my vehicles insured with Hagerty and have been for many years. I drive them all the time in rotation.
I had a total loss fire claim on one vehicle about 4 years. Hagerty agreed the car was a total loss 4 days after the incident and I received a check for the total agreed value 14 days after. No questions asked.
It occurred on a local freeway at 1:30 in the afternoon on a Thursday. I was driving home from work.
The adjuster never asked why I was driving it, where I was going , or anything like that.
Not only that, my premiums on all vehicles didn't go up after the claim.
The policy is worded very vaguely to include "pleasure driving". Every time I get behind the wheel of one of my vehicles, it's a pleasure.
If something happens and you're questioned, you just performed a tune-up and were taking it on a test drive, checking out the new shocks, making sure the brakes were up to snuff, etc.
I've never heard of any of the companies checking odometer readings yearly or anything like that.