The most question to ask yourself when buying a collectible car: Do I love it? Because despite the promise of many an eBay Motors ad, only a small percentage of cars are guaranteed to appreciate. Speculating on autos is more art than science, so we’re not going to recommend cars that you should buy and stash in the hopes of tripling your money (even though Historic Automobile Group International calculates that the value of "exceptional historic cars" has increased 163% since 2005).
These 12 cars are once we love so much want the pink slips before everyone else realizes how fantastic they are. They are surprisingly affordable, and special in some way. Some are more obvious (Lamborghinis will always be Lamborghinis), some obscure (an early nineties Mercedes sedan? Really, Maxim?), but all deserve your consideration. Find one you love, and start enjoying it before the wild winds of the collector car market blow it beyond your grasp.