I was in the same boat and decided to go the cross route. Picked up a Lemond Poprad for a very good price in Windsor, $500 off retail. You should be able to get a good deal on any in stock cross bikes because it's the offseason and they've probably been sitting on these bikes for quite a while. If you're in the Windsor area let me know and I can give you further details. I shopped around a lot.
The jake is nice but the components aren't great. The jake the snake on the other hand is a very nice bike. If you want to get close to a road bike the components on the jake are going to let you down.