Island hopping through the Gulf would be bad enough . . . imagine a winter Atlantic gale in that thing, navigating by a hand held GPS (I assume) . . . eating MREs, relieving in buckets, and hoping to God the engine does not give out. You could not just plop a stooge into it like a shorter run IMO, you need someone who can problem solve (at least a bit) and that person should figure out how bad it will be for the trip.
I mean, I can figure out one source of pilot/crews.
'You slept with el Jefe's daughter muchacho . . . normally he would flay a man alive who did that, but we need you to pilot this sub . . . get across 5 times and el Jefe said he would forgive you.'
Interesting part is, I assume the subs would be shipped back as cargo due to it being safer = RoI. Also, what keeps a narcosub like this from being towed by a freighter and being released off shore from where its to make the clandestine delivery.