I too recently had to go through that rigamarole with various classic
car insurers. In my case, I had no garage but I keep the vehicle at at
a friend's garage. This was acceptable to some companies but not
others. Iwas all set to go with American Hobbyist Insurance and was
shot down because my regular car was "too old"". They thought a 1979
Ford F100 as a primary vehicle was not sufficiently modern to be
reliable and that I would be driving the Cadillac as a second car.

I finally added the Cadillac to my regular auto insurance policy with
a stated value of $40,000. The company is Cotton States and they
required photos, etc. They told me their research supports the $40,000
value and agreed to insure it. The cost was triple what the specialty
companies quoted but at least it's covered now.