Anyone ever ride this old one? And are the younger ones really better rides, or just sexier?

The differences in bike technology and frame advancement even in the last 5 years is night and day.  As the guys who run my old shop say, it is not really worth it to buy an older model bike unless you are totally on a budget and get a great deal.  Because getting a $1,200 bike now versus spending $800-ish on something a few years older (even with better components) is not going to result in you getting a better bike.

I always coveted a 2300 when I first got into cycling back in '91 or so, but before I knew anything about bikes.  The early Trek carbon was like riding a noodle and you could not get power down to save your life.

If it works for you guys, no need to spend money to upgrade to something better.  BUT ...... if you guys did decide to upgrade it would be a world of difference ........

I also upgraded this year from a 1991 Bianchi to a 2008 Madone.  The Bianchi was stock, with 105 components, except for clip on bars and the triple I converted about 10 years ago.  The Madone runs the Ultegra SL components and I added clip on bars again.

The biggest differences I found were weight (about 10 pounds different) and having the shifters integrated in the brakes rather than the downtube.  I think the latter made the bigger difference.  I do know that after I got the seat adjusted right, I added about 2 mph to my usual ride.  It's definitely a much prettier ride as well.

Given that your shifters are already integrated, and you have carbon fiber tubing, I don't know how much more you would get from upgrading the bike altogether.  You'll probably get a lot more advice to get a tri-specific bike, so if there is a LBS that carries them, test ride a few to see if it handles differently for you. But I would suggest getting some clip-ons right away and practice riding with them.

Oooh cool. I have a Cannondale that's a bit older and came with 105 indexed downtube shifters. I wanted to bring it up to an 8 speed (from a 6), so it now has the same shifters as yours, except I think they are the Ultegra level. They look exactly the same though. I ride the Cannondale in the winter and like the feel of these levers better than the newer style Shimano levers. I have small hands though.

Anyway, she is really pretty.