I will provide my 2 cents as I am also in Toronto and have been slowly updating my wardrobe over the past year:
Suits – Take the time to research what a good fitting suit looks like wrt to shoulders, chest, length, balance, etc. Also evaluate what suits you have and what gaps you are looking to fill. Navy and Dark grey/charcoal first if you don’t already have ones you are happy with.
If you can find a good deal on a decent half or fully canvassed suit at a local brick & mortar, and the fit is good based on your research of what a proper suit should fit like, by all means get it and tailor it to make it even better. In Toronto, the markup at Holt’s or Harry’s is absurd in my opinion. Give Brooks Brothers a shot too, as prices and quality are alright.
SuitSupply is a decent option coming soon to Toronto. The quality to price ratio is surprisingly high from what I’ve seen. SuitSupply offers MTM as well, as does forum member Kent Wang who provides probably the best value around for a fully canvassed MTM suit.
Nothing of course beats the customizability and fit of bespoke. I as well have looked and am not happy with local bespoke options in Toronto – not a fan of the house styles (I favour the A&S and Neopolitan take). The alternative is to travel to NYC and consider a local or travelling tailor as they have an abundance of both. I don’t think this is viable though unless you have other reasons to be visiting NYC every 3-6 months for fittings.
If you are patient and don't mind some risk, quality items pop up here on the Buy & Sell and of course on ebay. Look into return policies and ensure accuracy of the stated measurements.
Prices with online MTM shirts are low in comparison to trousers and suits, so in my opinion it’s worth the risk even if several iterations are required before dialing in the right fit. I’ve used both moderntailor and Luxire with great success.
Most men who opt for no break are comfortable with a little bit of sock showing when walking. Provided the leg opening is sufficiently small this looks fine in my opinion. If you like no break, no cuff and want no sock to show, you can ask your tailor to do a slanted or military hem that slopes downwards slightly from front to back. This is apparently a much trickier and costly alteration if you prefer cuffs and is generally not done.
Allen Edmonds are a good entry-level goodyear-welted shoe. The Park Ave in black and Strand in Walnut or brown would cover most situations. Depending on your daily work wear, you may want to consider some more casual bluchers in brown calf, suede, or shell instead of or in addition to the Strands to better work with odd trousers. Alden has some great shell options. If you have the budget, some may advocate for jumping into the mid-tier directly (Crocket & Jones, Carmina), which has pros and cons.
Hope that helps,
<Edited: forgot about Brooks Brothers>