I get the hesitation, but honestly, classic policies can be a decent deal if your driving habits match up. A few years back, I had an older Mustang—my weekend cruiser—and switched to a classic policy to save some cash. At first, I was worried about mileage limits too, but it turned out I rarely hit the cap anyway. The key was being realistic about how much I'd actually drive it.
As for the coverage gaps, yeah, that's definitely something to watch out for. But in my case, the car was garaged most of the time, so weather damage wasn't a huge concern. If your neighbor parks outside or uses the car more regularly, I can see why he'd feel uneasy. It's really about matching your situation to the policy rather than just chasing lower premiums. Might not be worth it for everyone, but if your driving style fits, the savings can be pretty nice.