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.