I would like to see some pics of topping lift lines connection to the boom. Mine is a loop of rope and seems very homemade.
@John Tubb
Here is a pic of my topping lift connection. I wanted an adjustable TL so I got some small blocks and made a 2-1 arrangement. At first I tied it off to the horn cleat. I then added the clam cleat with line keeper. When sailing I loosen it enough to let the TL hang behind the leach of the sail. A bit of overkill but works well.
When I first got the boat there was a carabiner clip hanging from the TL. It connected to a shackle on the boom and when sailing I clipped it to the aft stay.
You mentioned your centerboard was stuck up. I had that problem for the first couple of years. Would stick in the up position unless I left it down 6".
Thought the CB had swelled so sanded it down real good. No joy.
No swelling within the CB trunk.
Then found a V cut into the tube where the pendant came out. Thought the thicker part of the splice for the shackle to CB connection was sticking. Got a high tech line with splice which didn't have the long thicker section of a standard splice. No joy.
So I had a local machine shop fix me up with a SS insert with flared end which I epoxied into the bottom of the tube. No more V cut. To install it I had the yard raise the boat's cradle an additional 1' so I could really inspect the inside of the trunk. While installing the insert I noticed a scratch on the side of the trunk just below the pendant tube (see pic 2). I checked the shackle and clevis pin and found the clevis pin had been cut down from a longer pin AND it was too long! Just a few mm's too long but with the taper of the top of the trunk, the pin would get stuck before the board was all the way up. Had to get a new shackle from D&R Marine to get the correct pin (see pic 3)
One other thing to add to your list to check is the thru hull and valve for the galley sink drain. Mine had a gate valve, which I understand was standard on O'days back then. With a gate valve you cannot tell if it is open or close. I had mine replaced with a gate valve and I am glad I did. The inside valve of the gate valve was completely gone.
As for a bilge pump, I don't have one and don't see the need. Only one underwater thru hull which is kept closed unless needed. Rain water leaks kept to a minimum. I use the galley ice box for dry storage so no water from that.
Any water I find in the bilge can easily be sponged out.
If you had an inboard with a shaft going through the hull, then you would have nuisance water to get rid of but you don't. To me it seems like work, expense and maintenance for something with little pay back.
On boats with inboard motors you do need one as most shaft stuffing boxes depend on water to keep the stuffing cool so you get constant dripping into the bilge. On our boats with outboards, I just don't see the need.
The only time I found my bilge almost full was one winter when a freeze/thaw cycle cracked the cockpit drain thru hull, allowing thawed water to go into the bilge. I remove my battery so a bilge pump wouldn't have helped that.
Sounds like your son is now your boat driver and you both are having fun. Great!