Given the current LCBO listings, I think it makes sense to break your potential choices down into the following categories (yes, you may have to go over budget):
HIGHLANDAberlour 16YO - $89.95
Aberlour a'bunadh Cask Strength - $94.95
Glenfarclas 105 Cask Strength - $79.95
Glenfarclas 15YO - $84.95
Hard to go wrong here. They're all excellent whiskies, and they all display a rounded Sherry cask influence. The 16YO Aberlour is the most nuanced of the bunch, the Glenfarclas 105 the most in-your-face and the a'buandh an absolute 'Sherry bomb'.
HIGHLAND COASTALOban 14YO (200ml) - $29.95
Old Pulteney 12YO - $79.95
I intentionally separated these two from the Highland/Island categories, as they're what I'd term ideal 'crossover' malts, lying somewhere between those two classifications. The OP's a little overpriced despite its quality. Plus you're wanting to broaden your horizons on a budget, so to speak. Therefore, the smaller bottle of Oban it is.
ISLANDHighland Park 12YO - $59.95
Talisker 10YO (200ml) - $21.95
The HP 12 is a classic Orkney malt well worth acquiring. But the option of purchasing a smaller bottle of the Talisker seems awfully attractive, too.
CAMPBELTOWNSpringbank 12YO Cask Strength - $99.95
Springbank 10YO - $79.95
Longrow CV - $79.95
None of these are exactly cheap, but what a distillery! The Longrow will give you a solid dose of industrial-like smokiness alongside its fruity sweetness if you wish to go that route, while the Springbanks are slightly more nuanced. Hard choices here. Many rave about the 12YO CS Springbank.
ISLAYArdbeg 10YO - $99.95
Lagavulin 16Y0 (200ml) - $33.95
Laphroaig 10YO - $84.95
Laphroaig Quarter Cask - $64.95
On a budget and limited to one bottle? The Laphroaig QC then makes a lot of sense. However, the option of trying the Lagavulin in a smaller format is also a tad interesting. Personally, I'd choose the Ardbeg. But then it's $10 less expensive here in Quebec.
LOWLANDAuchentoshan Three Wood - $71.95
You really don't have too much choice here. The LCBO does carry Glenkinchie, but it's never been a personal favourite. So you may just have to 'suffer' the Sherry wood influence of the Three Wood and be done with it for now. By the way, this price is also on the high side compared to my locality (alas, currently out of stock here in Quebec). Perhaps, it might be worth considering (as has been mentioned above) a gentler Southern Highland malt as a substitute for a Lowlander. I believe the LCBO lists the 12YO Glengoyne at a pretty reasonable price, and that would make some sense.
MIXTURE (ISLAY-HIGHLAND)Compass Box The Peat Monster - $62.20
A blend of malts from Ardmore, Caol Ila and Laphroaig. Good whisky. Good price. Good compromise if you're seeking a not-over-the-top peat-reeked blended malt that combines the attributes of two different regions.
The Yamazaki 12YO is all too drinkable.
Happy hunting!
