Originally Posted by Brushy

2. Drop bars: I've never ridden a bike with them. When I test ride bikes with them I feel a bit awkward, which goes against the 'does the bike FEEL right' question. But it's not the bike so much as my inexperience. I don't want to go with flat bars because that's what I'm used to and regret it because I'll feel like they'll hold me back. Advice?

Get what is comfortable for you. The advantage of drop bars are the multiple hand positions and more aero riding positions. With flat bars you can always get bar ends for multiple and positions and aero bars for an aero position. There are also non-drop bars available like the Titec Jones H bar that offer multiple positions.

3. Building your own. This totally interests me. But is it too much to take on as a total noob? Also, does the finished product really come in under the price of just buying a complete?

A complete bike usually comes in cheaper than building from scratch. Building from scratch is nice when you are picky about having just the right components and have the time, tools and skill to build it yourself. Keep in mind that pretty much everything on a bike is replaceable though...you can always modify a store-bought complete bike.

4. What the heck is this triple talk?

Triple front chain rings = more gear ratio options and usually more lower (climbing) gears.

6. Bad weather: I figure there will be times when I'm stuck riding in bad weather for sure. Like if it looks nice so I ride in and then it turns to rain when it's time to ride home... should this = disc brakes?

Unless you are constantly riding in bad weather, rim brakes are adequate...but discs are more reliable in wet conditions

7. Used bikes: One of you suggested getting a used bike and upgrading it and adding stuff. I've looked on Kijiji (Ottawa) and I'm not sure how to tell if a bike is worth upgrading or if it's just junk. Is there brands I should look for?

I'd recommend a new bike, from a local bike shop where you will not only get maintenance support, but also the opportunity to build a good relationship for your future needs.