How is buying extra crates than ones provided free at the start a bad thing? Didn't say they would be priced high, and even so you get lot of gold in the game anyway that 50 per crate is nothing....
That way you don't have to sail half way across the map to get new crates and have to sail back to other side to deliver the animals. Either way, cancelling a merchant and starting over in both scenarios is easily best thing to do unless its a 3-4 gold animal delivery. Then, I'd prefer 50 gold per crate than sailing far to other outposts just to sail back.
But, why are you buying the new crates? Because you've lost your old ones, which is effectively an additional tax on being sunk/robbed.
I'm not against the merchant just giving them out for free, my suggestion of only having one set available at each outpost was to make that a bit more structured and stop people just filling up on an infinite supply of crates in a matter of a few minutes.
If you are buying crates then you are having to sail somewhere afterwards anyway, and with two outposts always being close to each other I don't see that it would become an issue unless you were sunk twice, at which point you'd still have an out if you really wanted to finish the mission (and you'd have likely spawned closer to a distant outpost than the one you are aiming for anyway).
Again, no point getting caught up in details of a theoretical system, there are countless ways for Rare to implement it that would allow players to more easily recover crates without having to pay for it and without allowing people to swamp the game with items causing lag on the server (certainly saw it done in videos of the Beta, but it took work).
Just seen the patch notes. Thanks goodness for underwater gunpowder barrel damage. I think I've twice shot someone holding gunpowder and still had to deal with them afterwards.
(Bet it happens to me first before I get a kill from it!)