MY OH MY!!

I have a Devinci. I used to get comments all the time about "You don't see those very often."
 Nope - it's not a Trek, a Specialized, a KHS or a Cervelo.  It doesn't have carbon forks.  It has bottom end Sora components.  It's been awesome for me though - I ride it to work year round, I race on it, I train on it. I bought what I could afford and what I liked.  It's comfortable and I know I can spend hours on it comfortably.  I've had it 8 years and put goodness-knows how many miles on it.

People told me when I was first looking to buy the best I could afford - and used was a better option because you can usually get better components on a better frame for less $. I ended up buying new because it was pretty and the right colours.  I didn't realize then what a difference components and accessories make.  Best decision on my part? Nope - but I got lucky.  I'm looking for a new bike now and I won't make the same mistake.  I know I can get more for my money if I buy used - it just might take a little longer...

It might take some looking to find what you want - and take your time - you have until the spring right?

Basically you want to be comfortable on it. You're going to be spending a fair amount of time in the saddle and you want to make sure it fits.  Personally I would want to ride it - instead of ordering on-line - but everything can be changed - so I guess that might be an option.   

I've learned that everyone has an opinion about brands, but bottom line is that you have to like it enough to ride it ... a lot. 

After my first triathlon - on my old mountain bike, I inhereted a 15 year old Cannondale.  It was an awesome bike in it's time.  Aluminium frame, durace components, but it has shifters on the down tube, and it's quite old.  I put new tires and a new seat on it, and have ridden it over 6000 miles in training and several sprints, olys, a 1/2 IM, and a couple of bike tours.  It's a very good bike - although very dated.  I've trained on it for IronMan this year.

I'd suggest that you are right - look for a good used bike, it can carry you a long way.

I just bought a high end Kuota tri bike, and it is indeed an awesome improvement, but the Cannondale cost me ~ $100 for parts, and has been a super bike, and I've really enjoyed riding it.

Have you looked at places like swap meets and salvation army?

If you could just pay about $800 instead of $500, it would open up a whole new world of bikes to you.  Skip going out to dinner 5 or 6 times, and you will cover the difference.

Go to you Local Bike Shop (LBS).  Ask the employees if any of them have a bike that they are looking to get rid of.  That can work out to be a great bargain.

I was told when I was looking that a used bike is usually about half of the new price.

The Sora components were the entry level when I bought my bike.  Tiagra was one step up, then Ultegra and then Dura-Ace.  I've never had any trouble with my Soras - I've taken really good care of the bike and I keep it clean. 

Here's some stuff I found:

http://www.roadbikereview.com/cat/latest-bikes/road-bike/trek/PRD_290760_5668crx.aspx

http://kingston.kijiji.ca/c-buy-and-sell-sports-bikes-43cm-Trek-1000-Road-Bike-2005-Model-W0QQAdIdZ69882216

Seems the 1000s are going for about 450-550$. 

I just bought an older bike on Craigslist for $300.  A Felt F1 w/ Shimano Dura Ace parts. It is a real lightweight aluminum w/ a carbon fork and fit me perfect.  It was a good deal.  I don't know if I just got lucky.  I would keep looking and looking.  But I had to buy clipless pedals, shoes, a new seat and I am still looking for an aerobar.  And I set it up on a used trainer from CL ($30). 

 When I am done, I figure I will of spend a total of $800.  Actually my mom offered to buy me all the extras listed above for my bday and xmas.... So I really only spent $330...But you get the picture. 

 Hopefully, my boyfriend buys me some cycling clothes too!!! And pays all my race entry fees (j/k)!!!

I am real happy with the decision to get an older bike instead of a cheap new bike.   It has character. 

 Best wishes!