I ordered my equipment from a vendor in Montreal and it was shipped to my address in the US via UPS, so this is not quite the same situation as yours:
Q1 & Q2: The receiver was sent in the original box, unwrapped, (red, with "Shaw Direct" logo and the model number of the receiver plastered all over it. The only thing that had been removed from the exterior of the box was the bar code. I'm not sure what this bar code contained.....serial number, maybe? But there was no attempt to hide the contents of the box.
Q3: can't help you with this one
Q4: I had to pay a "customs brokerage fee" to the UPS man on delivery (so you want to be home when it arrives......use the UPS Internet tracking for the hour of delivery). The fee was about $30, but that included the receiver and the dish. Not sure what it would have been if it had been the receiver alone.
Now, I'm not sure if the vendor had some special way of getting it thru customs, but from all outward appearances, it had been shipped via UPS directly from Montreal, as the UPS Internet tracking system followed it all the way. It took about 10 calendar days to arrive.