I don't know how many times I have crossed the border to the US, both pre and post 911, but it is never much of an issue. "Citizenship?, where are you going?, How long away?"; "Canadian, Bills game, an afternoon", are simple answers.
However, crossing as a professional horseplayer is a different story.
A friend of mine is off for a month long vacation throughout the US. His trip is pretty cool - Mountaineer, Chicago area for some riverboat poker, St. Louis for the same, Oaklawn Park for racing, then across to Vegas for a couple of weeks. Crossing the border should be easy, but it was not. Why? He is a winning horseplayer, and apparently even border guards do not believe there is such a thing as a winning horseplayer.
When he was asked what he did for a living he said (the truth) "bet the horses and play poker". Red flag. Or for our Quebec readers, flag rouge. Just who is this guy? "Pull over sir."
So he was asked to park, was interviewed by several guards, had his car searched and was finally let go.
There is a lesson to be learned in this, I think. One, never say you are going on a a holiday to those places as a single man. They will think you are lying, or up to no good, or both. Two, never say you are a professional horseplayer. It is pretty clear that no one believes you can possibly win at the track so you must be engaging in tomfoolery.