"Well, this is why Oofta is wrong when he says I'm a rules lawyer, because I am using the feature but at the same time having it make sense. I'm not just throwing it out it entirely as being illogical."
As I mentioned above, I'd use the feature but make the PC establish those contacts first. Is that too "magical" or "illogical" for your tastes?
Unless you're trying to claim now there are no thieves' guilds--or anything like a thieves' guild--in Ravenloft, and you're unwilling to establish one, of course. If you're trying to claim the former, then it means you're unfamiliar with the Red Vardo Trading Company from 2e and 3x, which was a criminal organization hiding under a legitimate traveling merchant business (it's
based in Barovia, and has wide reach and influence), or are refusing to bring in anything from a previous edition. If that's the case, or you're refusing to establish a guild in Barovia--or even have some thieves from another domain happen to be in Barovia--then it means you're going out of your way to screw the players over.
"Oh, but Barovia is some small, podunk country! It's too small to have criminals!" you might say. Well, it's been a while since I looked at CoS, but I recall there being a lot of wine, and an entire sub-plot taking place in a winery. I remember that one because it was one of the few times I used a battlemat. Alcohol suggests the possibility of rum runners--people smuggling that wine to other domains. Or even people making bootleg wine, using grapes cultivated from seeds stolen from that winery. I seem to recall that, historically, illicit booze and organized crime often go hand in hand.
So tell me, is using pre-5e lore "magical" or "illogical"? Is creating a base of criminals of some sort somewhere in the domain "magical" or "illogical"? Is letting the party come into contact with them, so that the criminal PC has the option of starting a relationship with them too "magical" or "illogical"? Is this rum-runner idea--one of
several possible Barovian thieves' guild ideas I came up with literally in the space of a minute--too "magical" or "illogical" for you?