I am not going to miss another season, but I own too many bikes to buy another. Trying to figure out which bike would be better suited so a newbie CX racer (cat4 Roadie though).
In one corner I have a 06 Kona Dew Deluxe w/Nashbar Carbon CX Fork
And in the other corner, a 04(?) Giant NRS Air. Weird frameset I know, but it has good components.
I'm leaning towards the Kona, because it's lighter, simpler and the brake levers are already switched. If I put back on the trail tires it came with (no mud in NorCal during Sept-Dec), it's not so unlike the Kona Jake I used to own for commuting, just heavier (mainly wheels) with flat bars. Oh yeah, and the Dw can stop, unlike the Jake.
definitely the dew deluxe. it's a pretty nice bike. We sell them at the shop where I work and I often think about cross when I see them. Once we did a Dr. Dew up with cross tires and it just looked ready to roll! you could probably do a whole season on it.
Excuse my ignorance, but why not just buy a cyclocross bike? They're the best suited for cross racing, no matter what level you're at. Also, given that you're a roadie, the position would be more natural for you.
If, on the other hand, you want a bike to cross train in the winter, get a mountain bike! Hybrid bikes are always compromises: you cant race mountain bike races with them, and you may not be able to race in a true cross race with them due to the bar configeration.