Looking For First Road Bike

As the title suggests I'm looking to get my first road bike. I have a little bit of knowledge which could get me into trouble so I thought I'd get some additional thoughts. A bit of background; I've ridden bikes since I was a kid and am currently doing a bike commute (approx. 3km) 10 months of the year on a single speed. Since January I have been training for a 90km road race on a TT / Triathlon loaner from a family member. I don't think I'll be looking to complete any triathlons or looking to compete seriously. I'd like to find something that will be better than entry level but could upgrade in the future.

Your level of experience with cycling: Lots of casual riding, been training for a 90km race for 6 months.

What's your price range, and have you considered second hand?

Second hand would be fine, willing to spend $2000-$2500 CDN

What's your intention with the bike - commuting, fitness, touring, sport, etc?

Likely will be mainly for fitness, but would like to be able to do a 3 - 4 hour ride comfortably, or enter an occasional race with the intentions of being able to finish, not looking to seriously compete.

How far will you be riding, and how often? Anywhere from 60 - 100km, 3+ times a week

Riding conditions: roads, pavement, trails, single-track, off-road? Flat or hilly? Traffic and weather.

Roads and pavement, mix of flat and hills. I live in the foot hills of the Rocky Mountains. Likely would be riding on highways or city bike paths.

Your location (even approximate) can help other locals familiar with your conditions, too.

Calgary, AB, CAN

A bit about yourself: height, weight, and level of fitness can all help people understand your needs better.

5'11/178cm tall; 155lbs/70kg; above average fitness