Bottom line here is, Alan did his homework and with the help of professionals (non-TFers, likely) got LEOs on both sides onboard.Custom's Officers have a lot of power, and don't take kindly to anyone not following the rules. Oh, and you are supposed to know the rules, not knowing is not an excuse.
I'd bet the question of re-entry was already decided and documented before they left.
We're not giving Alan and his crew, credit for thinking at a higher level than the average social media addict.