First off can I ask why you are looking at a vecile that is riding on what is prbably the oldest platform in the car industry? The XC90 was long in tooth 5 years ago and little has changed aside from some decontenting. That aside my comments are below:
I looked into the US overseas program when I bought my 2006 V70R so about 5 years ago. At that time the "official" word was that the US oversea delivery program was for US residents only. If you have the paperwork to go around this ( PO box in the US?) then perhaps you can make it work. Have the program requirements changed? Typical Volvo garbage on the US/Cdn. pricing.
Pricing details to consider:
-You will pay 6% on the Volvo when importing into Canada.
-Volvo was being real sticky with the clearence letters. Last I heard the Canadian dealers would provide them after a $1000+ inspection.
-Some minor RIV fees etc ($500 total)
-Lastly there was some complaints that Canadian dealers would put US spec vehicles to the back of the list when it came time for warranty issues/customer complaints. They would fit you in, a few months down the road.
Also beware that Volvo began putting MPH only on some of the US models rather than the dual scale setup. To make it legal for Canada would require a complete gauge swap ($200k + ?) or perhaps the old 70's solution of adding km/h stickers to the mph guage cluster.