Keeping a WWP14 in the water?

[SantaCruzin]

Well...of course plans have changed. After spending the last 2 months refinishing my WWP14 (stripping all of the bottom paint, multiple coats of primer and topside paint) in anticipation of never needing to have the boat in the water for an extended period, I now have the option to get my boat in the Santa Cruz harbor. This leads me to a few questions:
1. Has anyone here kept an older WWP in the water for extended periods? If so, how did it do? Besides the obvious bottom paint, I'm just a bit worried about the continuous moisture given the age of the boat. I did just repaint the cabin, cockpit, and deck along with the hull but still...it's an old boat with a LOT of wood.
2. Now that I have a nice clean topside paint job on the hull, how might I go back to bottom paint if I go that route? Currently, the hull has two coats of bottom paint primer and two coats of topside paint. Would I need some form of barrier paint before doing an ablative bottom paint?
3. How would I go about protecting the daggerboard and trunk? Should I drop the daggerboard, clean it up, and coat it? Should I be worried about the trunk? I painted as far in there as I could when I redid the bottom.