The 101 sub-article is located in the Styleforum 101 link in the top bar, and there is a somewhat short description of footwear. There are also some good links at the bottom of the article.
Most people on here also recommend that you follow WAYWRN: Shoe and Boot Edition, and try to figure out what you like.
In Toronto your best option might be Brooks Brothers, who sell rebranded Alden, Allen-Edmonds, and Crockett and Jones footwear, and $600 affords the majority of options. Harry Rosen carries a limited selection of AE shoes, along with other brands such a Ferragamo (I think AE is HR's only SF approved brand).
Another standard piece of SF advice is to buy two pairs of AE shoes (AE ships to Canada, and Nordstrom has regular sales on them, down to $220 per pair,) as starters, along with a set of shoe trees, and other shoe care goods, so that you can give the shoes a 24 hour break between wears, though this may not apply to you if you are not wearing the shoes on a daily basis. The AE appreciation thread is a great source for pictures of their shoes, and most other SF-recommended shoe brands have their own threads (Carmina, Crockett and Jones, Alden (located in SW&D), Gaziano & Girling, etc.).
P.S. Make very certain you get your shoe sizing correct, or else you may make a very painful and expensive mistake, this is one good reason to get at least your first pair(s) of shoes from a local store.