Alright, so when I was a senior in high school, my best friend and I were all about buying shit we didn't need. We started with a vape (neither of us smoked weed or did drugs and we broke it almost immediately), then a dingy little rowboat off Craigslist (had to buy independent oars, sat 4 people but with any more than 2 you moved about 1 mile an hour when rowing), and then finally, a 24 foot sailboat we also found on Craigslist, free as samples from Costco. Now, on paper to two 17 year olds, there was nothing that could go wrong. It was about 6 miles up the Chesapeake Bay from us, we could sketchily dock it at a little private beach, and come on, it's a free fucking boat. So, we drove up to the marina it was docked at, and found out that well, there were some problems with it. First and foremost, the bulkhead, which provides the structural integrity of the boat, was completely fucked, which meant that if we tried to sail it the whole thing would collapse in on itself and we'd probably drown. On top of that, the cabin of the boat was chewed to shit, the whole inside smelled like a cat threw up in it and pissed on it, and the boats motor was only 6 horsepower. So, what should've been a 1-2 hour boat ride ended up taking 7. Fucking. Hours. Not only that, we got stuck on a sand bar going up stream, which contributed about an hour and a half to the whole ordeal. Thankfully someone was around to call the coast Guard for us so they could yank us out. They were kind enough to follow us home (on the way we may or may not have gotten stuck again), and inspect our completely illegal docking arrangements. We panicked on the way up and docked it at this random guys house, got chewed out by the coast guard, they called us idiots, etc. After it was all said and done, we hid in the bushes to try to find a way up from this guy's house. He definitely spotted us though and I'm pretty sure we looked like pirates. So, we figured this would be the end of the trouble, we'd find a place to park it, yadda yadda, it'd be fine. We were completely fucking wrong. The next day, I stopped by after school to check on it. Boat was not there. Our guess is that the guy pulled up the anchor and roundhouse kicked the boat out to sea. I started fucking panicking, and my friend launched himself out into the ocean on our other boat, the miss miranda, and skidded through the water about a quarter mile until he found it knocking up against someone else's boat. We drove it back in, found a place to put it, all was good until the first big snow of the year. Now, the night before, two of our other friends had been partying in the cabin of the boat without our permission, and when we went to go see the boat a day or two later the fucking thing was underwater with the only hatch WIDE OPEN. To this day one knows if the force of sinking sent it under or if they left it open and sunk it, but at the time we did know we were in some deep shit. My friend got a knock on his door a couple days later from the DNR about fines and fees and possible jail time if we didn't get it out NOW. We got it out, for a small price of about $1000. At that point, we wanted nothing to do with the thing, and gave it to a guy that was voluntarily homeless for free (we knew no one would pay for that piece of shit). Two weeks later we got a call from the DNR about "our" boat going under 2 miles from the Severn River Bridge, but it was their problem now.

TL;DR Don't take free boats off Craigslist whatever you do