This is the coolest thread on pinside right now, and it's keeping me from wanting to chop my legs off at work to get a couple sick days in. It makes me feel like some ultra fiscally responsible person knowing I've never bought a fire truck, some gyrocopter, or other uselessly amazing things, but I know I'm not because I have 12 pinball machines in my basement.
I bought a Sunfish sailboat once on craigslist for like $500 though. It even came with a trailer. I didn't even know how to sail it, and I didn't have any car with a hitch, but I thought "Eh... Looks cool. Maybe I'll get people to call me Captain Ahab or something."
I sailed it like twice, ran into something because I was clueless, and punched a hole in the bottom. On top of all that, people haven't started me calling me Captain Ahab either. Maybe it's because I don't have a beard, or maybe it's because a sunfish is basically a canoe with a sail. Idk. Either way, it was fun.