'Yellow Flagging' works if you don't get caught! "Right of Passage' works when you are sailing past, not anchored. Chances of getting caught are small but fines can be high for any immigration infraction and some of the Islands are very sensitive about the rules. It is their interpretation, not your's, that will be applied.
You are only 4 days sailing from Grenada
. We did it 2 yrs ago with 12 to 24 hr jumps and 2-4 day stays. Islands like Guadalupe let you check in at the internet
cafe and most of the others are not onerous to check into. We are heading to Bonaire
from the USVI on the same schedule and we don't intend to leave for 2 weeks.
When tropical storms and hurricanes threaten the only sensible thing is to get the boat into the best hurricane hole you can find and get ashore and into a concrete building well above the possible storm surge.