Matt - Sailing from Jost I'd say you should anchor in Dewey and clear-in. That's different than coming in from the USVI.
You're really supposed to do this when coming in from the USVI, but on occasion I've been able to "streamline" the process.
On Flamenco - Even in the summer in settled weather it's generally rolly. Swell comes around the point. We anchor there every time because we're usually in a large cat, and we love the place, but in a monohill you'd probably get thrashed pretty badly.