I'd probably start either by moving him into his own bed in a familiar location or move him into the shared room in the cot, not both at the same time if that makes sense? One change at a time kind of thing, get him used to the first one and wait till he's comfortable, then introduce the next change - I'd also try get onto it sooner rather than later (I'm assuming there's a timeframe with the new bub coming?) so it's not as likely that he'd associate the changes with the arrival of the new baby.
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