I understand what OP is getting at. I haven't watched Summit, if he were to post a constructive thread here himself instead of what I assume is just complaining to his fans I would happily weigh up his concerns.
I enjoy a wide spectrum of activities on SOT, I would say that my play style is well balanced between social, pve and pvp elements.
For me it is not that I want extra loot from people doing a Tall Tales. My problem is if I do decide on nefarious activities that result in the sinking of another vessel and then find out that the cargo is tall tales; I'm immediately taken out of the pirate fantasy. Because I'm ridden with guilt. Especially since the decision to engage on another ship is not always my own depending on the crew I find myself sailing with.
There is no value in sinking someone on a Tall Tale (at least most of the times I've unfortunately done it). And even if there is, as in they have other cargo, I don't want to spoil that great content for anyone, as in forcing them to restart the tale again. I would end up sailing around the world looking for the crew to return their items probably...
In one of the tall tales, you obtain an item that is accessible through the equipment wheel. My solution would be to make all keys and Tall Tale related items that cannot be sold into non-physical items that are accessible by any crew member.
This way if you happen to get sunk while on one, you can still complete it after you get your new ship. Making it a minor inconvenience to both ships, rather than outright wasting both crews time.