Skyguy9999 on 12/9/2010 10:09:26 PM:
You have the biggest thing about riding down. Many "legit" cyclists take spinning classes to try to improve themselves (specifically speed/cadence), and if you've been teaching it for 8 years, you're way ahead of the curve.
The best bike for the Katy is as the others say, a hybrid or road bike, but consider the other riding you wish to do (road, harder trails - the Katy is basically flat, cyclocross?) as well as the kind and weight of the gear you wish to carry. Different terrain has different demands on gear, as well as whether you plan to camp or just light travel. My suggestion is to also get a professional bike fitting if possible (i'll explain why later).
As I see it for other issues, Trek hints well at one of them. Learn basic maintenance well (fixing flats, adjusting brakes, and your handlebars and seat), and carry the necessary tools you need to do these things on your rides. Nothing sucks more than to be 5 or 10 miles (more on other rides besides the Katy) away from civilization and have no way to get help other than to hike the rest of your day out. It's just a fact of life - it will happen and eventually you will need to deal with it. You need to learn how.
The only other factor that will concern you is the long ride times. You are like already ahead of the curve *somewhat* in conditioning, but a long ride is more like a marathon than a sprint and you will need to learn how to deal with those. This will include seat time of those long durations to condition your muscles and backside to be used to it. As well, you will learn whether the fit of your bike is good or not (see above). Your bike may be fine in the first 30 minutes, but even a small error in fit will show up in 4-5 hours and can be very painful.