Mostly because getting a 5$ item through canadian customs will end up costing me 25$ of additional charges. But I might order a bunch (I do have buddies with the same problem) to make charges less ridiculous.
A few things I've found:
First off, don't go near UPS for this. They have a "brokerage fee" that they slap on anything they move. FedEx wasn't doing it, but may have started to. No idea as to DHL's routine.
Secondly, get the item sent by US mail (USPS). If it's tagged as priority mail, I think it switches to a delivery company once it crosses the border, but no extra fees (I believe). Typically the sender has to fill out a declaration form and list contents and value. I just normally have a value of $5-10 put on it. No receipt in the box helps too...
Thirdly, if all else fails, ship to someone in the US who will drop in the regular mail for you and put "gift-stuffed animals", "free product sample" or the like on it.
Some retailers don't show USPS shipping, so a quick phone call might sort it out for you too. There are a few ways if you are a company on the receiving end as well I think....
For example, I just shipped up a bunch of handheld radios by USPS and no issues whatosever. It even arrived at my company's office instead of my PO box which I normally use.
It's not that I have a problem paying appropriate duty on items, just a "fee" charged by the shipping company (UPS mostly) for no reason, and making money by calling it something related to the government regs. Bring a car in, hazardous materials, livestock etc., no problem with a broker's fee, at least the first time. After I see the paperwork trail, I'll do it myself.
Of course you could get it drop-shipped to the closest town across the border from you, drive over and then back. Declare it at the border (hold up the bag of small stuff), and get waived through. Thanks to NAFTA/others, most things are duty-free/excise tax exempt anyways.
See if that helps,
Sir Veyor