For many of our couriers, taking this at face value is sort of frustrating. For one, the Courier does not seem to be a homebody. Some dialogue suggests he/she does not know where she was born, and a lot of dialogue, particularly in Lonesome Road, suggests that he/she frequently travels and can't stay put for long. Also, if the Courier had a big role in creating a big and successful wasteland settlement, why the hell does he/she not know what the hell Ulysses is talking about in the DLC? If something like that is added to our character that late in the game, it's just so frustratingly vague. At the same time, however, that's the best part about it. The Courier is given the option of saying that Ulysses is just assuming, but in my opinion, it sort of makes him seem like even more of a misguided lunatic than he already is.
Now, he is known for speaking figuratively. My take is that when he's saying "you" created the town, forged the roads, he's not talking about the Courier individually. Instead, "you" is people like the Courier. People travelling to settlements, making them thrive. People with jobs like caravaneers, couriers, and mercenaries. In that way, our player character very much helped create the town. They don't have to be a frontier settler, sheriff, mayor, or what have you, they can just be what much of the game implies: a wandering, travelling, drifter. A Courier without a home. To me, it's extremely fitting.
I may not have conveyed my point as well as, say, Longknife, but what do you guys think? What are your interpretations of the info given by Lonesome Road?