With the Mysterybox being changed, I'm wondering if any of the vending machines are vending Keelhauliday items at all?

It's not a vending machine, but the changes to Maleria has her giving out occasional Freyalise items as prizes.

Thanks for letting me know! :)

Ocean Depths. :)

Thank you! I've been super sick for the last 3 days so I am behind on pirating things up. :D

You just need some patience when vending there. I've had some good luck getting a few items about 12-13 out of spending 1.5k tokens over a range of 3 days.

On a similar note, pirate items are also possible to obtain (at least rarely now) through Maleria quests (she gave me a very good one).

Not only Maleria, I've been getting pirate items from the Library quests as well.