I bought a bmw z4 used with very low mileage, and sold it for slightly more than I paid for it about 14 months later. The reasons I was able to do this:
1. The age of the car seems to disproportionately affect the depreciation, so you don't end up paying extra for very low miles. But when you sell it you can hold out based on this. It also gives you a cushion of miles you can drive it without affecting the value. As long as it's below some arbitrary "miles per year" the buyer has in their mind as reasonable, it works out.
2. The new models had come out, with a starting value a full 50% higher than the previous models. So my used one, while still being super fun to drive, was a vastly cheaper option, so alot more buyers could be interested.
I still lost money on the deal, as the markets were roaring and that money wasn't invested.
I'm glad I did it when I did. I had a ton of fun driving that car. But it was just that, for fun. I got it out of my system. If I did end up with a massive amount of cash for some reason in the future, I'd consider it again, but that's only if I had a level of wealth that let me own my own racetrack as well.
Tires: Every 7 years might be right, but likely your first set will be sooner. Also, they aren't necessarily just a little bit more expensive. Each individual tire on the z4 was as much as a set of tires on the truck I had before. If you plan to hold on for awhile, tire shopping becomes like every other expensive thing, you keep an eye on it and watch for deals.
Cops: You aren't getting a warning. As an obviously rich SoB you are getting a ticket.
Gas: My fuel costs went down, as the z4 got 39 mpg when I wasn't zooming. Most fuel efficient car I've ever owned, only car I had to pay a "gas guzzler tax" when I bought. Of course, the worst mileage I ever got was less than one mile per gallon, when I was, um, lets just say, exploring the boundaries of my commute time at 4 a.m.
Other people: There's gonna be commentary. I tried not to let it get to me, but it did.
Enjoy it! If it stops being fun you aren't stuck.