One anti-theft policy will be enough. It's almost impossible to satisfy the conditions and actually get a payout from any of them, so having only one will mean that you only have the frustration of getting turned down once instead of twice. There's no point in paying for two insurance policies that will never pay you a dime anyway; one payout of $0 is the same as two payouts of $0.
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Work: the 8 hours that separates bike rides.