let’s ignore the sailor here, because that is a completely different case and worded completely differently…
The problem with your ‘ought to succeed’ and ignoring what the world looks like is that it is the world that gets in the way of it succeeding, so your ‘I care about a logical game’ bit ignores the world it takes place in, which is a large part of why anything would be considered logical or not
So all you really care about is whether it is consistent with your interpretation of the rules, not with the world, at which point your
becomes empty posturing
Either you have to consider the world as described to achieve logic and consistency or they are not all that important after all. You cannot just ignore the world because it would be convenient for you and claim logic and consistency are not affected by that
So to get rid of the cop out (you do like those..) of ‘every world is different, so I ignore it in my answer’, let’s go with the Ravenloft as described by me. Vistani can travel the mists, they can decide what other domain in Ravenloft they go to (unlike anyone else…), but they can never leave Ravenloft.
Your character is from some other world and did not know of the existence of the Vistani, but has the criminal background.
In Ravenloft, you now meet a group of Vistani for the first time. Do these Vistani meet the description of messengers you know from the feature? If they do, can they get a message to your contact? If so, how likely do you think it is that the Vistani agree and that the message makes it to your contact?