Milage-limited insurance over here is pretty much standard. It's pretty simple: You submit the mileage when you start the policy, and if you get into trouble with a higher mileage on the odo than you should have, they void your coveragemake you pay the difference plus a penalty.
That sounds terrible. I usually have recreational insurance on the Miata and set it to something like 6k miles. What if my friend invites me to an unplanned weekend roadtrip down to the Tail of the Dragon and I go 200 miles over or something. Why do I need to pay a penalty for something so insignificant.
I never quite understood Boss 302, it's much slower than a Shelby and not much faster than a normal GT but costs noticeably more. I can (somewhat) understand track day specials on something like a Porsche or a Lambo/Fezza as they are essentially toys for rich people. But on an every day car like Mustang doesn't seem to make much sense, you could turn a normal GT into a Boss 302 for way less (and even retain factory warranty).
Ummm, the Boss and the Shelby are two totally different cars with two different purposes. Even though the Boss has 218 less ponies under the hood, it will outperform the Shelby in any competition except a straight line drag race. The 662hp in that GT500 is simply too much for the chassis and the car is pretty much useless. Having driven both, I'd take the Boss 302 any day without even a 2nd thought.
And the Boss was never meant to be used as a daily, much like the more expensive track toy specials you mention. Its just that due to its price point, people end up using them as dailys, and I don't blame them, I would too.
As for turning a regular GT into a Boss, its easy, but not significantly cheaper (if we use a new 2013/14 GT price, not used). And you'll actually void the warranty on a bunch of components, so I wouldn't recommend it if you're planning on relying on the warranty.
Even if we bring the 2015/16 GT into the mix, I'd still probably end up choosing the Boss. While the updated interior and the IRS are huge improvements, I just still think it feels less spirited than my GT.