BTW, I sent you a PM regarding a used bike.

Complete Allez E5 with Sora 9-speed for $1250 is about right...But, you can find used Allez's in good condition, less than 7 years old for half that. Just some food for thought.

For an example:

Allez Specialized Road Bike - 56cm Frame - Mint Condition | road | Oakville / Halton Region | Kijiji

Not half the price, but two years old. Much better componentry.

I'd be open to purchasing a used bike as long as I can get the right sizing for me! I have no problems with saving that much money, lol. Unfortunately, I'm unable to see your PM, until I hit 10 posts. I've bookmarked that used one that you've linked here and am going to contact him tonight. Thank you!

What is your height? Here's the link from the PM:

2013 Giant TCR | road | City of Toronto | Kijiji

I just hope my computer is not already irretrievably infected by your virus

I'm 5'8, or 5'9 if your my doctor, lol.

Haha! Unless you're the CEO of a conglomerate, I'll leave you alone...

You'd be looking at a 53, 54 perhaps, but depending on the geometry of the bike that 52 cm Giant I cited might just be your size.

Where are you located anyway?

I live in London; I'm about an hour and a half away from Toronto. I see that Giant comes with the Shimano 105 groupset. I guess that's another perk of buying used! I'm going to check out the bike shop sometime this week and check out what sizing/style I'll be looking at for the handle bars. I'm hoping to make the purchase in the next week or two. The weather is looking great here for commuting!

I don't know if this is legit, but here's another one that might fit you. Quite under priced for that bike. It's Mississauga so not quite as far a trip for you.

2014 Giant TCR | road | Mississauga / Peel Region | Kijiji

The used market is nowhere near as robust for bikes in London as it is in the GTA.

Haha! I'm actually planning to be in Chicago this fall... I don't think that I can be so patient though! Yep, our dollar is pretty bad right now, but I'm about to check a few sources now; we'll see!

Thread too long, didn't read....

Check out Urbane Cyclist on College Street, they're a dealer for All-City bikes and they have some pretty decent cross models.

Canada eh? I live in the Shwa.
My own opinion is that a more upright posture will allow you to see more. Maybe you are lucky and get to ride lake O bike trail most of the way.
So in the spirit of the Toronto style commuter bike:
Opus Classico $550 CDN
Opus Zermatt less than $800 for sure and has disc brakes.
Both are about 33lbs with not fat tires and have fenders and racks.

There are a few other bikes in that segment. Most really good bike shops for that style are in Toronto but Bicycles Plus in Whitby does sell these commuters.
Urbane is a really good shop, Toronto has a few and kijiji is full of bikes.
There is also an ultra-light version of this bike on the site.

PS: bike reflector and light laws changed this year and I don't see much in the bike shops to allow compliance. Fines are up too.