What are in minnesota? would help to search Craigslist.

$2500 is a good budget to get into cycling. You'll find alot on cold weather riding in that forum. Those guys can help you get stuff to ride in.

Dont rule out ebay....I saw a nice 2010 Orbea with 105 components going for $800, but I dont know what size you need.......
If you are only interested in the Trek vs. Cannondale I would go with the TREK 2 series...I have never been a cannondale fan.