Player: MadsAP
Character: Akachi Imari
If you take part 2 of the pirate kobold cove quest ( the sailing part ) and you fail it by the boat running aground, your journal updates with a failure but also makes you unable to get a reward for part 1.
It seems odd you loose the part 1 success reward by failing part 2. I'm guessing it's a bug, because I still had the invite tool after the journal update. (Or it's just a bug that it's not removed when it fails)
No bug here. It is explicitly stated that you risk quest completion by taking the second part. Which you should, as that is the cool part of it.
The option for Part 2 explicitly warns you that to attempt it is to gamble the success of your quest.
Double or nothing!
Ah, I must have missed that part in the text.
That still leaves us with the invite tool being left in inventory, although a very minor inconvenience.
Is it just random whether or not you run aground or catch them or do factors play in, like sailing skill?
There are both factors and randomness involved, with inclination towards success rather than failure. Sometimes you just have pure misfortune though. Locking as there are no bugs, may look into removing quest invite tool.
Praying to Besheba may or may not be a factor. Umberlee too.