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I'm not suggesting hiring a van is of itself sufficient, it is Darren Osborne's combination of actions that should have resulted in him being pulled over.
Chains of related events are easy to spot after the event. Beforehand, the exact same chain of events may have led to entirely different outcomes.
Post hoc reasoning is no way to run an intelligence service. Thankfully.
They monitor people who are already known, and for those that aren't, they look for stuff that's a bit more obvious than hiring a van and driving to a different city. Otherwise you'd have armed police swooping in every time someone bought a sofa off eBay.