Yes, getting her down could cost almost as much as buying her. Sam, my sailing and backpacking buddy, will come with me to help out. Don't think there's anyone here really close to Medina (near Cleveland), and wouldn't want to roust help this time of year anyway unless I had no alternative.
The trailer she's on is not roadworthy. I spent $700 to redo lights, brakes and tires on the borrowed trailer that's taken Windward coastal for the past 4 years, and not looking to drop anything like that on a one-shot use. A second trip would add another couple of hundred $ in gas to the party. Plus, the owner says the trailer scares the heck out of him, and he doesn't go over 40 with it.
I'd love to have a trailer that would handle Windward. I stupidly passed up a chance to get one locally about 6 years ago. It would have taken some fab work to permit proper adjustment, but was reasonably priced, in good shape and I knew the owner. No accounting for poor decisions some times
I have pics of the boat on the trailer, and the owner is getting dimensions for me. Beam is close to Windward's although she will sit higher due to the fixed keel. I have access to taller screw jacks than the ones that are on the trailer now, and if necessary can knock together some cradle-like cross-braces side to side between the pads if they don't support the hull adequately. I can keep the locally borrowed trailer for as long as I need it, so the first round of work can happen in front of my house instead of in the water. Not wild about doing a bottom job when it's really cold, but I can wait for a warm spell and do any interior and hardware work in the mean time.
We may consider blocking and jacking the boat, yanking the old trailer and backing in the new one, but I've found a marine service yard with a crane that will do the transfer at their hourly rate. If I have everything adjusted close before they fire up their gear, I bet we can keep it to an hour. A couple of hours of their time is worth it to avoid a "hold my beer and watch this" situation jacking up a 3000# boat.
At least this provides some stimulating activity during this normally relaxed holiday, end-of-year season.
