First, it would be helpful to know exactly which Crossrip model that your comparing with the Steilacoom model. As I perused both the Trek and Diamondback websites, it would appear that the base model of the Steilacoom is much better than the Crossrip base model. I mean 105 vs. Claris, 8 speed vs. 10 speed, carbon fork vs. aluminum etc...
Also, if you're going to be cycling mostly on paved city surfaces and just a few moderately wooded trails, you could get a really nice performance hybrid for $1000. I'm thinking like perhaps a Jamis Coda Elite, a Giant Seek or Escape, a Raleigh Cadent, a Cannondale Quick SL 2, or a Trek 7.5FX.
However, if your mind is set on a CX bike, then the Steilacoom is gonna be hard to beat!
