Zinn and the Art of Road Bike Maint. is probably the most user friendly, helpful and 'chock full of good info' book out there IMHO. I've also made a binder of printed out pages from the Park Tools and Sheldon Brown sites for my own reference.
As for road side repairs. I made sure that all of the repairs that I envisioned doing could actually be accomplished with the tools I had on the bike, not the tools in the big tool box at home. I found that my multi-tool allen wrench couldn't reach one of the allen head bolts that secure my rack, so I make sure to pack an allen wrench that does fit. (hint, I painted my day-glow orange for when it gets dropped) I also discovered that if you use SRAM powerlinks (great invention), it's not a bad idea to pack an extra one. They do tend to disappear when they slip from your tired greasy sweaty fingers into the grass.
An extra piece of coathanger type wire bent into a wide "U" shape is great for holding both ends of the chain and giving you some slack to work with
Hope this helps.
Steve W