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GlassDog · 46-50, M
He could have arrived at the town limits at 11:59:59pm on Friday night. By the time he got to his hotel, it would have been Saturday. If he stayed five days, that would have taken him up to Thursday, and if he was slow leaving the town (i.e. leaving at 11:59:59pm on Thursday night), it would be Friday again by the time he got back to the edge of the town.
I know it's not the answer you wanted, but it was a bit of lateral thinking.
I know it's not the answer you wanted, but it was a bit of lateral thinking.