Just to help clear up some confusion in this thread, I have Maryland "historic" tags on an old Mazda that I used to use for drag racing and hardly ever drive anymore. My Jeep is an '06, so obviously it doesn't qualify yet. There are NO mileage or time restrictions on historic tags from the state. The ONLY thing you have to do to get the tags is prove that the vehicle is at least 20 model years old if the model is no longer in production (if the model is still in production (like say a Ford Mustang) it must be 25 model years old. I do not know if they would consider a YJ wrangler to be still in production since a JK is still technically considered a Wrangler - keep in mind I was getting the tags for an old Mazda 323. After that, the only thing you have to do is sign a waiver that says that the vehicle receiving the tags is not your primary means of transportation (i.e. not a daily driver). Then you pay the fee and pick up the tags.
I have heard that if a cop notices you driving a vehicle with historic tags frequently that they can pull you over for it - for example if they sit in the same spot every day and notice you drive by every day, but I don't know if that's true but the tags don't really stick out so I can't imagine it would be a huge deal.
I don't know about your insurance company, but I have Progressive and I called to notify them that I was putting historic tags on the car and asked if that changed anything with their policy and the girl laughed and said they really don't care and it doesn't change anything on their end, but I can't speak for any other insurance companies.