Cyberspeed- I think your summer scheduling might be the best time for both Maughan and I. He'll need a good advance notice, and I'll need a little time to finish and test my rudder swap. I've yanked my old rudders, 'glassed the inside of the transmoms with thick woven-roving, and am grinding and filling the gelcoat cracks from when the Dotan housing twisted off. I've got some TheMightyHobie18 housings but still need to buy new blades for them.
I've been planning on buying a new set of sails for this summer anyhow, and am already saving up. All of my standing and running rigging is recent and has few hours on it, all of my blocks have been replaced and are working nicely. I went through those systems last summer.

I do have a Cheeta motor mount on my boat, but haven't yet got an engine for it. I'll get looking for some 2.5-4HP kickers, but was also thinking of setting my boat up for oars. It's too wide for a single person to row from the center (tried it before) but it would be fine for two people to each take an oar.
As for capsizing possibilities, I guess I should order one of Gary's Solo~Rights sooner rather than later

After all, I don't know if Maughan and I are fat enough to right my boat when it's got a few extra pounds of gear onboard.
I have also been thinking about putting a tri-color and VHF antenna at the top of my mast. I could easily store a deep-cycle battery and VHF radio in a box in front of my mast on the forward trampoline. Mostly, these are all things I could borrow off my Seafarer 24 sailboat...
Pete Bollard- I've been thinking about sailing from Tampa Bay to Dry Tortugas this Spring Break (March 20-28). I know it's not crossing the Stream, but it should let me put enough miles under the keel to figure out which systems need to be tweaked.