Cool, I'm looking into doing the same thing.
1 gal water jugs work good. Even better with an extra empty 5 gal collapsable tank like those sold in camping supplies. with a clean tarp, and funnel to capture rain water.
On some of those boats the swing keel has a locking bolt to keep from undeploying during rough seas. If it doesn't think about building one.
Upgraded rigging, and reinforced mast step should take care of most issues, every boat of every size has it's weaknesses.
Locking pins on hatches, and hatch boards, drains on cockpit lockers, seals on lazeret lids,....
And with a solid hull, and good ballast ratio, it should be just fine, after all you will be "coastal sailing", and can escape major storms if you watch the weather.
That size of boat will fit in ICW easily, and is an option if it gets too nasty offshore.
I'm also working on a "pocket sailer", and I hope to meet you in the Carribean someday. :thumbs up:
The Sun has Risen on a New Day filled with the Promise of Adventure.