Enterprise. Nimble and very agile, plenty of room inside and usually local racing if you want it. Plus there loads of them about. Older plywood boats better than old GRP ones. Bow bulkhead a must have to stop nose diving after a capsize.
I'd go for the power winch. A non-tiring source of grunt can prove very useful. Sending people up the rig, hauling the boat alongside when you've mucked up the approach, etc. As well as hoisting the mainsail especially after shaking out a reef.
My boat has powered primaries. Necessary...
What about things deliberately jettisoned?
When I gave up smoking about 500 miles off Bermuda on the way to the Azores, my faithful Zippo lighter and an ashtray that had been on family boats for decades, went swimming, No chance of recovery from the abyssal plain.
I've been at the opposite end. I bought a boat from a guy who was swallowing the anchor. It came laden down with piles of rubbish. Several sets of his grand children's finger paintings, Loads of spares for an old engine that had been replaced, enough pyrotechnics for a municipal firework...
Buy a cheap one design for winter sailing. I bought a Flying Fifteen a few years ago, December through March at Grafham Water SC for 2 people and boat park costs £155. 3 races back to back on a Sunday.
My Yanmar takes a surprising amount of cranking before it deigns to start. It's an indirect injection engine with no glow plugs IRRC. It's probably the worst starting diesel I've owned.