A few years experiance.
Several years ago, I purchased a J/24 racing sailboat. It has a 4' keel, and a keel stepped 37' mast. It weighs just under 3000lbs. It can be single handed, but at the same time it takes 5 if you want to launch the spinnaker and go racing.
I spent the first summer trying to figure out how to launch the boat. With the keel, many of the local ramps didn't have deep enough water to launch the boat - even with a 20' tongue extension. Once I actually lost the trailer at the top of the ramp, and it raced down the ramp on it's own. Luckily, no one was hurt, and I was able to retrieve the trailer with a line, after swimming out to it. The trailer that came with the boat was closer to a dock stand and was never meant to float the boat off.
The next summer I spent learning how to raise and lower the mast, and rig the boat. Luckily I had a couple invites to Annapolis to race on a friends J/24, and by taking many pictures, I figured it all out. I finally rented a slip on an annual basis on Kerr Lake, NC. I didn't have a motor, and got stuck a couple times with no wind. I bought a used motor, but it had a bad waterpump, and would overheat. After waiting over a month at the shop, last summer I finally got going with the repaired motor. Someone stole my spinnaker pole at the dock - guess I was too trusting leaving it topside.
Eventually, I got some good sailing in. At first, I wanted a way to reef the sails in high winds (over 12), but learned that the J/24 has all kinds of controls to shape the sails for the available wind. I learned to sail the boat flat for better speed. My friends & family finally began to sail with me some, trusting that I might know what I was doing at this point. Unfortunately, this year they raised the slip fees up to $1700/yr, and I decided to pull it out. It took part of a day to pull it, and part of the next day to unstep the mast, and get it ready for traveling.
I love sailing. But my experiance has been that it's a lot of work, and it's just enough "off the beaten path" that many of your otherwise good friends may not participate in the adventure.
I'm thinking I'll spend a month or so to clean up the boat, and get it ready to be sold, and then perhaps buy a boat that's easier to daysail, with a deck stepped mast. A J/22 may be in my future.
Just wanted to share my experiance.
Wow. Sound like a pretty challenging couple of years. Glad you haven't given up entirely.
You may want to check out the recent thread here called "What boat after learning basics." That fellow is moving up, while you appear to be moving down in size, but a lot of good ideas about trailer sailing and slightly smaller boats appeared there. Check it out and good luck.
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