I bought my first Grady (my third boat) - a 2007 222 Fisherman - virtually site unseen. I live in southeast North Carolina, and the boat was just south of Tampa. To this day it was the nicest and newest of the five boats I have owned. Not the nicest in terms of the overall package, but the nicest in terms of condition. It was one of those deals that you just have to jump on. The guy made an off-handed comment on THT that he was thinking about selling it. I PM'd him, he quoted me a stupid low price, and the next day (Monday) at 4pm (I had a work commitment earlier that day that I could not get out of) I was in my car barreling south with a cashier's check. I had asked him about the condition of the trailer, and he said it would certainly get me back to NC. He said they dragged the boat from Tampa to the Keys a lot and the trailer was fine. I did manage to get a Yamaha tech to stop by during the the day on Monday and look the engine over for me. I asked him to take a peak at the trailer for me as well, and he again said it would get me back to NC.
I drove overnight hitting a bunch of construction traffic and getting there about an hour before our designated 7am meeting time, which afforded me an hour of sleep at a rest stop. I met the seller at the marina, and the boat was as described. It was in great shape, new SIMRAD electronics, a strong running Yamaha 250, etc. The trailer, however, looked rough. I did not have that much experience with trailers at that point, but nothing looked like it was about to fall off, so I hit the "I believe" button and, after a quick sea trial, I had it loaded on the trailer to start heading back north.
Now, keep in mind I had another work obligation first thing Wednesday morning. I was just past Tampa on I-75 when I ran in to stopped dead traffic that lasted for hours. There was a fatal wreck just up ahead that had the road shut down. Once I passed that I got about another hour down the road (at this point I was cutting across the state on US-301) when I pulled over to top off the tank. The hub on one of the four tires was burning up. I consulted with a buddy by phone, found an AutoZone a little bit ahead of me, and greased it up good. I stopped a few times over the new few miles to check it, and all was fine. Or so I thought.
It was 5pm by the time I made it to the north side of Jacksonville, FL on I-95. I was waaaay behind schedule and facing a late night arrival back home, but I was back on the Interstate and moving along. Then, just north of Jacksonville I blew a tire. No swerving or anything like that. I just heard it and pulled off onto the side of I-95... near Jacksonville... at rush hour. I grab the "trailer and emergency" tool bag a buddy had given me. He runs trailers as part of his business, so I was grateful to have his pack. Well, it did not have a wrench in it big enough to take the nut off the spare tire that was bolted to the trailer. You have got to be kidding me! The bolt was too long to use the socket set, and the nut was too big for the crummy wrench he had in there. So, I had bought the Boat US towing coverage the day before, and I call them up. Local guy says it will be 1-2 hours before he can make it out. While I am waiting, I start trying to McGyver the bolt off. I manager to take a hammer and very gently tap on of the corners on the nut and, after some time I got it moving. 90 minutes later when the tow truck showed up, I was finishing putting the spare on. The look on the driver's face was priceless. He just pointed to the tire and gave me that "What the Hell Am I Doing Here?" look.
So now it is close to 7pm, and I am still in North Florida and out of spare tires. I look online and find a Walmart at one of the first exits on Georgia. I stop in, buy 2 more spares, get gas and food, and I am back on the road. Now it is after dark. I am so glad I bought two spares since I blew too more tires the rest of the way. I also had a check your pants moment when I came over the peak of the Santee bridge on I-95 only to find a tractor trailer stopped dead right in front of me, and I somehow managed to stop before I hit. I got home after 3am. Keep in mind I had been working on one hour of sleep in the past 44 hours. Also keep in mind I had a meeting I could not miss at 9am that morning and it was an hour drive from my house. If I didn't have that meeting, I would have stopped somewhere around the SC/GA border, checked into a hotel, got up in the morning, dropped the boat in at a public ramp, brought the trailer to the scrap yard, run the boat home on the ICW, and had my wife drive me back to get my truck. It was that brutal, but I had a great boat and I was home.
Now the best part. I never planned on keeping the trailer since the boat was going to be kept in a dry stack. I threw it up on Craigslist for $1,000. A guy showed up the day I listed it and bought it. No negotiation, and I would have negotiated. I discussed the issues I had with it on the drive back, and he said he didn't care cause he only really wanted the frame. He gave me the money, hooked it up, and left to drive it the 5-6 miles back to his house. He calls me 15 minutes later and exclaims that I must have a golden horseshoe shoved up my rear! When he got back to his house he saw that one of the wheels had fallen off during the short drive from my house. I don't mean one of the tires came unbolted. I mean one of the wheels broke off the axle! I told him I was more than willing to give him his money back, but he again said he didn't care since he only wanted the frame.
In the end, the seller only stated it would make it back to NC. He never promised it would go any farther!
I think back on that trip and both smile and cringe. I smile at the great story but cringe at all the dumb things I did and how much worse it could have been. I wound up selling that boat a year later for 1/3 more than I paid for it. I replaced it with a 273 Chase that was also down in Tampa. No trailering for me this time. I learned my lesson and paid a shipper!