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When my wife and I did the UHaul thing from the US, my biggest fear was that I'd end up in the middle of a Customs parking lot trying to repack that 3-D jigsaw puzzle.
Didn't happen. We just handed in our paperwork, answered some questions and drove home. From a border security standpoint, i'd have actually felt better if Customs had at least opened the trailer door.
The degree to which you searched and questioned depends on individual circumstances, attitude, and the mood of the Customs inspector.
With regard to your concern about entering Canada with a DUI, there shouldn't be a problem. Your PR card gives you the legal right to enter Canada.
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