I bought a 2005 T2000 for my tour of the Northern Tier during the summer of that year, and I had a difficult time finding a front rack that would mount on the "Fatty" front fork. Honestly, I feel it's a very limiting design that Cannondale should address. As you may note by the variety of responses, personal preferences are just that - very personal! From what I can see, the Jandd rack might be more successful, simply because the rack's bottom attachment point comes up from below and behind the drop-out eyelet on the fork. Due to the design of the fork, you might find that to be critical. Bruce Gordon makes great stuff, but before I spent the money on one of his racks, I'd check with him very carefully to see if the rack would work on the T2000, specifically at that point. It might require long bolts and spacers, which I'd want to avoid. As for my own experience, I ranted at Cannondale enough so that they gave me a fork for the T800, painted to match my bike - you can see how the forks differ on their webpage. A Tubus Tara slipped right onto it and provided a very solid and dependable rack. My personal preference is a low rider. The Tubus racks and Arkel Grand Tour panniers were an excellent set-up on the bike.
I'd be less concerned with heel-strike than with "toe-strike". If you turn at very slow speeds on the Cannondale - you're liable to hit the rear of the front wheel with your toe as you pedal on the down stroke. Just be mindful of it, and it shouldn't be an issue.
Have a great ride on the NT - you're in for a treat!