@Blondihacks - Here's how you might be able to get Pappy Van Winkle in Canada:
The Liquor Control Board of Ontario occasionally receives very small allocations of Pappy Van Winkle and other rare whiskies. They typically sell these through highly anticipated online lotteries or controlled allocations, which are announced well in advance. You'd need to register for their special releases or Vintages email lists to be notified. The prices, while higher than MSRP, are typically still much lower than the secondary market.
The Société des alcools du Québec operates similarly. They have product pages for Pappy Van Winkle 20 and 23-year-old, but typically show them as "Not available online. Not available in stores." This indicates they are released via specific, limited allocation events only.
The BC Liquor Stores also have a "Collectibles" program. Pappy Van Winkle is listed in their brochure at specified prices (e.g., $300 for 15-year, $500 for 20-year, $800 for 23-year), but these are usually released through highly competitive special draws or allocations.
In Alberta, where liquor retail is privatized, the AGLC manages distribution. Some private liquor stores in Alberta (like BSW Liquor or Liquor Barn often showing "Sold Out" or "Unavailable" might receive allocations. These stores often run their own lottery or waitlist systems.
In Manitoba the Manitoba Liquor Marts have explicitly held "Premium Spirit Release" online draws for Pappy Van Winkle and other highly sought-after bourbons, as recently as September-October 2024. This looks to me like the best mechanism for potential acquisition.
Similar to other provincial bodies, the NSLC in Nova Scotia manage any limited allocations they receive through a lottery or special release.
There are also Secondary Market / Auctions: This is where most of the Pappy Van Winkle available in Canada appears, but at VERY significantly inflated prices like 5-10k for a bottle! (HOLY CRAP!) For example, Waddington's in Ontario is an auction house that is permitted by the LCBO to consign and sell spirits in the secondary market in Ontario. Similarly, there are a few on-line outfits that carry it for many thousands of dollars.
Hope that helps. If I were you, I'd register with the 4 western provincial liquor control boards and wait for it to pop up. Hopefully tarriffs won't apply.