So it's my understanding that the 2005 models will be coming out in a month or so and that 2004s usually go on sale at this time.

What kind of sale should one expect (% wise)? Is it usually a gradual increase (starts of at $100 then after 1 week $200 so on and so forth) or is it a one time decrease and 1st come 1st serve to grab it?

As you can obviously see I'm a newb to all of this, got a hardtail mountain bike a few months back to commute to work (6 miles each way). I'm seeing a lot more pavement in my future (and not much trails) so I really wanted to get a quality road bike with as much bang for the buck that's possible.

Trek 22-2300 seems abou right...

Well i got my fuji one year ago. Msrp was 1999 and i think reg price was 1599 and i got it for 1099 as the 04's were getting near.

what are some good websites that have good deals on road bikes?

I have seen:
www.bikesmart.com
www.airbomb.com

I paid 1400 for a MSRP 2200 Street 1900 cannondale jakyll 800 reciently (04 model closeout)

I'm picking up a 2004 Fuji Professional this week for only $1725 walkout - I think that's pretty seriously discounted for end of year, and they had to order my size (64cm)!

Bikesdirect.com has some good deals on Ultegra level bikes in the $1K range. But you won't be able to ride them first.

You might want to look at the Trek 5000. If I'm not mistaken, isn't the 2000 series Alum frames? The 5000 is the same frame as the 52/5500 only with a lesser build. I think for the money, the 5000 is a much better buy than the 2300 (5000: lesser parts but superior frame).

Best.