Sorry, I missed this the other day.
I like that Skerry a lot. Good looking boat, nice sailplan, relatively easy to build (by accounts). Fun to sail, easily trailered/launched (even car-topped).
But I'm note sure I'd recommend the standard version for open ocean sailing such as you contemplate. While it is fairly stable, it is intended more as a coastal/bay/lake/river boat. There are some potential issues with capsize recovery that should be addressed, too (the top of the standard daggerboard trunk is low enough that it can make bailing out the swamped Skerry nearly impossible -- but there are remedies).
You might want to read David Bixby's account of a swamping he had in his Skerry, Bonnie Dune
. David is an experienced Skerry sailor and has spent a fair bit of time (before and since the incident) addressing capsize recovery issues: The Wreck of the Bonnie Dune
You may also wish to visit Steven Roberts' great Skerry forum at Get-Outside.com . Loads of experienced Skerry builders and sailors there.
All things considered, I think I would be more confident in our Passagemaker Dinghy in open waters. It is actually a "larger" boat than the Skerry (payload-wise), and is tremendously stable.