You wont be able to put cross tires on your road bike due to the clearance. I would just use a mountain bike, some say to change the tire to skinny ones but I never did when I tried first started. Just used an only Trek MTB and had fun.
I ride around the neighborhood on my bike all the time with flip-flops on. I don't think they affect anything with regular shoes and like freeride said, as long as you aren't like going balls out to the grocery store they will be fine. You might want to look at the crank brothers candy also...
Eggbeaters all the way. I run them on my XC bike and cross bike and they are by far the best pedals (I think). Other than that it looks really good. I wouldn't go with the gravity dropper post though unless your going to do more all-mountain riding.
I've always wanted to race track. My dad used to back in Detroit. He actually has a warm up suit from the Madison Board Track team. It looks like a lot of fun and takes a lot of strength and skill. Too bad the closest track to my house is all the way in Colorado Springs.
Eggbeaters all the way. I run them on my XC bike and my cross bike. I've never had any problems with them getting filled with mud.
Spend the money for stainless ones. They will hold up a bit better than the chromoly spindles.
Personally, I would not buy a used cross bike. They go through so much abuse depending on who has ridden it. Ridley is a very good brand though and like JRogers said, they are huge on the euro cross scene.
I'd think it through. There are a bunch of good cross bikes out there for under $1000 new.
I ride/race the Jamis Dakar XCR Pro. I love Jamis. The bikes feel great. I haven't ridden the XAM but the specs are nice and its a fair price. You get a good bike for the price.
As you can tell, I'm bias towards Jamis. I haven't ridden a Kona so I don't know how they are but I've heard fairly...