My experience was all positive and there were some pitfalls. To start with the owner reported the ship destroyed. It wasn't destroyed, just busted up a bit. I wrote to Transport Canada, explained the situation and requested they de-register it for export. Took about a month, then after I repaired it and signed off an annual inspection I requested the Airworthiness Certificate. Local FSDO asked if I wanted Standard or Experimental? I opted for Experimental, they came out, looked the bird over and typed out a Certificate on the spot. All this did take some time, but mostly because it needed to be repaired. Couldn't get an Airworthiness for Export, because she wasn't airworthy! Didn't need it anyway. If you want a Standard Airworthiness Certificate, you may have to pay a DAR to perform a compliance inspection to prove it is in compliance with its Type Certificate.
Much simpler to buy a ship here, but with a little patience and a good deal, I wouldn't hesitate to buy a Canadian bird.
JJ