slamdunk: I've def done this before. That questline's scripting is a tricky one. I just ate it as a loss. however, If you're familiar with editing InvenSource.mes I think maybe you could find the item id and get it to spawn in a shopkeeper's inventory but I can't recall if the behavior of quest items allows this.
edit: I poked around various game files, and I think the spawning trick won't work for this letter
Well, I returned to Tarant and reported back to Matt that I've read a note about change of location. So it's safe to say that reading the note before the actual quest is sufficient to have that follow-up dialogue line. [100%]
The problem may occur if the note is dropped from your backpack without prior reading. However that particular line in dialogue has no significance in terms of plot since it doesn't change anything, even the journal is not updated. So someone may assume that even in such dire circumstances the respected quest can be finished with no issues [not 100%]. But it also may be hardcoded to require a note inspection before spawning a plot character. This I'll not check because this game is long.
UPDATE: I just noticed that this dialogue line updates Journal's Rumors section. So it may be necessary to read that note after all. For some reason the journal was not marked with update after conversation with Matt.