Yes, I've thought of the iPod, but all I have is a shuffle

... It's my kids that have the 40Gig video versions

Also, I'd need an adapter, and not all of the boats have cassette decks. All the boats that I use have CD players.
RE: the
winch handle - I have found several times that I haven't needed it! However on the two occasions that I didn't, there wasn't one aboard...

I figure that one of the keys to being a good sailor is to be self-sufficient

Further,
WHEN I get my own boat, I plan on taking the
winch handle with me when I leave the boat... In a way, it's like taking your keys from the car when you park.