I am in Canada and have done a lot of transactions. Need a bit more info....
What are you buying? This will tell us size, price, fragility, etc.
Where are you located and where is the item? I am in Toronto and drove to Tennessee for a Pass Labs X350.5 at an amazing price. I also drove to Houston for a pair of speakers at an amazing price as well. For the right deal on the right item $300 for a return flight to pick up a high end CD player is not a difficult decision. It does cost an extra bit for land travel but I get to see my $10k used investment before my hard saved dollars are given. Why not? I get a smoking deal on a CD player $3k under market value that I have been looking for AND take an extra day in the visiting city as a mini vacation :)
As for fees/taxes I have found that the boarder doesn’t want to deal with this in person. The only time they pulled me over was pay tax on the X350.5 and they also bent the rules and took off the couple of hundred dollars off the value for being over the boarder more than 24hrs. When they released me the agent didn’t want to see the item, only the stamped paperwork from the inside agent that I was clear to leave.
If you ship it different story all together. Again need to know what you are shipping. If it is possible ship Canada Post. It is cheapest and least likely to receive any attention for extra taxes. Claim $400, $600, $800 good chance no taxes. Claim $3k good chance there will be taxes owing. Ship UPS, FedEX, DHL, etc expect a nice fat brokerage charge unless the sender pre-pays in advance and I can assure you that you will pay any taxes owing. Ensure they do, it is less than half the price. Way less.
The Houston trip was a pair of speakers 210lbs each. I rented a minivan through a website and the entire trip cost me $1k CAD. Speakers were $2k USD under fair market value. All expenses included plus I got a wonderful mini vacation O my goodness the US has some beautiful scenery and landscapes in areas. If I tried to ship it would have been the same price- $1k freight to Buffalo then I go get them (1.5hr drive one way, not bad). I got to audition the very expensive to replace drivers/repair speakers to ensure they were perfect.