Well for what it's worth here's my nickle in the juke-box,
What I want:
A working head. It's a much better and safer option than over the rail, and the bucket thing is just nasty.
A self-steering setup. even if it's just a sheet to line rig. Gonna be plenty of times I need to be away from the Helm to get things done.
Bookshelves. Love to read almost as much as I love Jazz.
Sound system. Don't need to be fancy. And if it fails, well the i-pod in my head will kick in.
Solid hull and rig. The best safety net is a good boat.
What I'm not worried about, but I'd like.
A destination. It gives you some impetus to get going and set your lines straight. But "The point of the Journey is not to arrive".
Radar. It sucks a bilge-load of juice, but if it even once keeps me from being run over....
A refrigerator. Would be nice, But I have no problems subsisting off of PB and 'taters. Plenty of dried' canned good to leaven it out.
A HAM rig. Makes it cheap to talk to my parental units, and if you can receive it, there's a net for just about everything.
Things I really don't care if I have or not.
Liferaft/epirb. It's just me. If I screw the pooch and wind up sinking my own boat, why shouldn't I pay the price for it?
Speed. I want to be in a given place in a hurry, sailing probably won't get me there in the most expeditious manner.