The most important question here is: Why the hell would you drive 11 hours for a Nascar pin? They are a dime a dozen in the midwest and are hard to sell from my experience. You should be able to find one in good shape , within an hour of your town, being so close to a large metro. city.
From my 15 years of experience, if you're not willing to shop around a bit (locally or at a show) for a decent game and view and play it in person, you get what you deserve every time. Shipping a pin is similar, from my experience. You have no control over how the game is treated and handled once it leaves your sight. I haven't shipped a game for over 10 years and I will never ship a game again.