Instead of dropping the anchor you can also take it to Smith on Mos Le'Harmless He'll repair it into a pretty neat looking weapon, Just make sure you have the The book o' piracy & like 300k on you aswel.
I remember damage soaking was a thing back when I did this quest and the battle with the Barrelchest is the only time I remember that mechanic kicking in for me
Fraqsu I try to stick with your guides over other content creators because of how clear and understandable you make them. I looked through your channel for a "summer's end" quest guide but couldn't find it, are you planning on doing this one? Thanks! :)
I'd say bank and get more food/supplies before final fight if you are lower combat and/or play on legacy combat because the boss hits hard and frequently.
Just a heads up you can take the charter directly to Mos Le'Harmless from Catherby, at least I think once you've started the quest (that's when I saw it, didn't pay attention the first time)