I am in Canada as well, I bought my first Rolex, an Explorer II in London Ontario. They were asking 5800.00 I talked them down to 5400.00 or something around there. Now, of course in Canada we have the lovely GST and PST. which on a 20 or 30 dollar item its no big deal, but at at the time another 15% onto 5400 and that put the watch over the 6000 mark!
From that day on, I vowed never to buy another Rolex in Canada. We vacation in Naples Florida each year where our family has a home and the Sales tax is only 6% in Collier county, so thats where I would be doing my shopping for watches. Not to mention the area is very wealthy and there are lots of stores that specialize in pre-owned watches and there are some really good deals to be found. I found a Submariner in Mint condition with Date selling for 3100.00 complete with all original packaging and papers. I know in Canada with taxes etc the cost will be close to 6000.
One of the stores in Naples told me they had over 2 million in Rolex inventory (they also employed an armed guard) and that Rolex sales make up 90% of their business and I saw 2 watches being sold while I was talking to the sales agent, so getting a deal there, I am sure is out of the question as they are selling these daily! In London Ontario I got a deal I assume because they were either overcharging in the first place, or sales were slow and they wanted to generate some cash flow. So your best bet for a price break might come from a dealer that doesnt sell as much volume, but then is the starting price going to be the same as what a high volume dealer would charge you with no deal?
Not to mention our Dollar is now on Par with the American. Personally, unless you find a great price in Canada, buying from the USA is the way to go! But dont use the mail or courier, because then you will get hit with customs and tax! Go to the states and wear it home!