Insurance and swaps.

As far as the insurance goes, I would contact Hagerty. There are a multitude of classic car insurance companies. Make sure you get a policy that is on "agreed" value not "stated" value no matter who you use. You and they agree to a value on the car and that's what they would pay if the car is totaled.

Also Hagerty will let you just go for a cruise in your car, some other companies don't.