I've got a Kona Jake set up with rack and fenders. I absolutely love it, though the stock tires (same as on Jake the Snake) are noticeably slower than the 25c Gatorskins I swapped on. The rack and fenders were both very easy to install -- no drilling or jerry-rigging required, all the mounts right where you'd want them.

One difference between Jake and Jake the Snake is that the Snake has a 46-36 double crankset while the base Jake has a 50-39-30 triple. If you've got troublesome hills you might want that 30t ring, and if you like to go fast you might want the 50t. On the other hand, the Snake's 105 component group is a nice upgrade over the Jake's Tiagra (although really I'm pretty happy with the Tiagras).

Both Jake and the Snake have Avid Shorty 4 brakes (nearly ubiquitous among cyclocross bikes) which I think are really weak as they come stock. I've read that putting on some real brake pads (e.g, Kool Stop) and/or switching to a shorter straddle cable will fix that, and I'm going to the LBS today after nearly being hit yesterday and seeing how bad it is at emergency stopping.

The rack mount points on the Sutra are rather strange. It makes me wonder how well it would co-operate with fenders. The geometry is a bit more relaxed than on the Jakes, which could be good or bad depending on your point of view.

The Raleigh Sojourn is a sweet bike. I don't personally like bar-end shifters, but that might be the only thing I'd want to change about that bike. The 11-34 cassette is a really wide range, and it makes me wonder how it would feel in practice, so that might be another thing that I'd change.