Maybe I'm not seeing how these checkpoints work, but twice now getting to the 3rd checkpoint in this Tall Tale where we've recieved the Counterweight, I'd have to stop. The first time, we just ran out of time. The second time, we were attacked by both a kraken and skeleton ship. (I play with my little kids, so they are not battle savvy). I can reload the checkpoint, and it reloads the pages to go to Sailers Bounty with the Counterweight, but it never shows up on the table so we no longer have that quest item. Both times I've tried to g0 re-dig it up, or change servers a couple times and reload the checkpoint again and it gives me everything except a new counterweight, forcing me to have to restart the entire quest. Am I missing where it shows up? I check the voyage table right where we all vote on to load the checkpoint.
Edit: To clarify, I'm referring to Trapmaker’s Gunpowder Key as the counter weight needed for the next stage.
Edit2: Figured it out. I will leave this here in case anyone stumbles across it. The end of the checkpoint stops right before finding the Gunpowder Key, so I needed to leave the game to spawn a new server, come back in, and do the final step and just dig up the key. Previously I didn't respawn a new server before trying this part. We just finished this Tall Tale finally tonight.
