I'm not sure what you mean by "always work" or what in my posts inspired this question.
That's kind of my point. If there are "blank spaces" that haven't been filled with enumerated details, what's wrong with letting the player add something?
Avoiding the whole "know someone" part of your statement, they'll be able to secure free passage if the player says they do. The exception would be when you don't need to. That, and that it isn't 100% certain to meet every need. The spirit is, you'll get free passage for the party when it matters to get to the place you need to go.
Yep, we disagree. One line of text isn't going to override how I approach D&D as a player or DM. I'm not going to argue about the rest.