2 of the 3 runs I've done for the 100% category have resulted in a glitch where the homeless man does not appear. Walking to a building that has an interior and then coming back (to essentially try to make the outside area reload) doesn't seem to work. There was one report of this happening online years ago but in that case, the character model was missing but you could still interact with him. This is different. You are unable to see or interact with him.

I just wanted to make this post as a warning/information thread since a cause hasn't been determined. It's hard to find something that I did different between the 3 runs that would possibly have made this happen so perhaps it's just random? Either way, I'll leave this here as a warning for anyone running this category and also maybe we'll add to the thread if we're able to figure out a cause and effect for this issue (as well as any troubleshooting of course).

I think I sent this to Droogie elsewhere, but for any newcomers: The Homeless Man glitch is caused by not picking up a town map. The easiest map to grab is either the one just before leaving the building after the train ride, or the one on the park bench by Dig Spot 1.