In the conversation at the beginning of High Road, Ulysses makes several references to how I formerly walked from west to east, and now I needed to walk back toward the setting sun. Yet in fact the path through the divide is west to east. This is confusing me. Also, I entered the divide from the east, but then walked through a fairly small silo and ended up at the extreme west edge of the map.

Does anyone else find that this DLC messes with their sense of direction?

There are many discussions about this DLC on the forums here and many interpretations. If you look at the Divide Map though, Ulysses temple is in the west and you have to walk towards it. It's like a large circle, first you head east, then you go through the Cave of the Abaddon, and when you come out, you should be heading west again.

I just like to think that my courier traveled to and from the Divide, but never paid it much attention. It was just a place for her. She made her deliveries and that was it. That's why she doesn't remember much about the place. East , west, what does it matter to a courier, who's used to walking the Mojave in any direction.