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I wonder if he may have met someone who was going off to uni or back to uni. University start dates are generally later in sept or early oct rather than school start dates which are early sept.
Student accommodation varies wildly in the UK, from shared apartments & houses to solo studio+ apartments, if you go for a private rental instead of university associated accommodation. This would give more cover potentially for a perp or associate. I knew plenty of people in university who had partners, siblings and even parents stay over in their shared university accommodation, but that leaves a lot of opportunity for someone to be found out.
I can speak from experience here as I actually started university in September 2007 exactly a week later from the day he went missing so one of the reasons the case sticks in my mind.