Hello, klepp0906.
This issue I have explained in the following quote:
As you correctly assumed, because "We Need a Shipwright" quest require to interact with the Garrison Flight Master too, the bot is clueless which of them is first or second in the gossip.
Will do my best to check for the next update if other gossip options are available to the Flight Master, so have stable workaround for this issue.
I guess you mentioning "Hook, Line, and... Sink Him!" quest. It is abit tricky, so better logic is need there, working for all scenarios.