I am looking to optimize my solo run of the Shroudbreaker tall tale. I was wondering if it would be against the rules to disconnect once I unlock the checkpoint for the Shroudbreaker item.

I know I could just sink my ship while on the final island but that is not a 100% chance it will spawn at an outpost. It isn't clarified very well in the rules so I was just wondering.

So are you saying you go through the tale, and once you get to the final checkpoint you disconnect, join a new server, continue from your checkpoint on the new server, and turn in the fresh spawned item at that outpost? So long as you have unlocked that checkpoint during the run and the run doesn't start from a checkpoint, I think we should be okay with that, yeah.

Yes, that is exactly what I'm saying, Thank you for the quick reply. :)

Yeah I was thinking about doing the same thing as you. I'm not sure if it's actually faster than sending your ship to an outpost while you're on Crook's Hollow. One thing is sure it's load dependant and you could end up on an awful outpost (Dagger's or Golden Sand) so it might not be that much faster overall.