After further review, I see that my documentation was not the best on the centerboard. Regardless, photographs I have are attached. They document when I bought the boat and cleaned it up.
I replaced the lines and cleaned up the hull and it came out pretty decent. I copied the existing CB teak piece using Jatoba wood, which worked well. Unfortunately, I let it weather so here I am doing it again. Not complete yet, still need to finish the woodwork, buy some new rope, and screw it into place. Some thoughts:
Initially I dropped the boat in water to rotate the CB and pull it out. This time I'm contemplating just attaching the trailer to my truck, sliding the boat back on the trailer just a bit to clear a crossbeam on the trailer, jacking up the trailer and placing blocking under each wheel to get enough clearance to rotate the CB and pull it out. I'm thinking 18-20" under each wheel should be enough. Sounds scary, but I think I have the right gear to do it safely.
The rope is easy to replace and just knots on either end in a recess of the CB. My centerboard had some chipping and separation as well. I'll try to repair with some resin this go round. My CB slid in and out easily for the repair.
My hull seems to have spread a bit when I bought the boat, misaligning the door to the cuddy cabin. Hasn't gotten worse since I bought it though. I reworked the lock to make it functional and moved on. It's more cosmetic as far as I can see and doesn't seemed to have affected the structural integrity of the boat.
The original teak piece had split and I pretty much just duplicated it. I should have made some changes. My change this time is to make the entire piece wider to make sure the wood doesn't split where the screws attach it to the hull. My original fix split over time. You can increase overall width maybe 3/4 of an inch and it will still fit on the center well. Only the area where you split the cuddy has to be near original width. Keep it as wide as you can to avoid splitting. I don't have a picture of my original finished job, but I'm going to brag on myself and say it looked pretty darn good.
Instead of natural wood I'm going to try composite deck material from Lowes. Much cheaper than teak or jatoba and easy to work. Built for bad weather and doesn't need finishing. See the attached photo I just took with my original fix on the left, my first try in middle, a raw piece of deck on the right. I made a routing error in a lower hole on the first try piece (see the lower rope hole) so I'm going to try one more time. The decking is too thick so you'll need to plane it. I left mine a bit thicker and recessed some of the hardware to get it to work. If you're proficient to some degree in woodworking this piece is not hard but it takes time.
Some of my original screw holes were stripped out, where the teak attached to the hull. I refilled them with resin, drilled new pilot holes, then made a template out of 1/8 plexiglass so I could see exactly where to drill holes. It worked well and my new piece, when done, should fit perfectly. I could send you a paper copy of the template rolled up perhaps.
As far as sailing, I'm a rookie and have sailed no other boats. I will tell you that I have had a lot of fun sailing this boat and I find it easy. I even flipped it over once and was able to right it by myself.