The Bar Towel

I noticed there was detailed information on importing liquor purchased across the border, e.g. in Buffalo.

Has anyone had any experience importing a personal wine cellar across the US/Canada border?

I have a wine cellar ~ approx 500 bottles - the majority of which are not carried by the LCBO - which I'd like to bring over from my residence in the US to Canada. Has anyone had experience dealing with Canada Customs or can provide me with any insight as to the process?

My questions specifically include:
1- legal ramifications
2- taxes and duties (of which I'd like to avoid if possible ~ avg cost of bottles $50~100 USD)

I've never had experience bringing a personal cellar across the border. I would definitely suggest calling ahead to arrange something like this. Give Canada Customs a ring, and also the LCBO - when I was researching the costs of bringing beer over the border they were more helpful (and accurate) than Canada Customs ever was.