1. If the check points are passed then when the player passes the crossing line increases a lap. If they haven't passed all check points then the lap won't increase.
2. Sparkys collision is probably the easiest I've used. Well, it's actually the only one I've used so far. The terrain would be setup as a complex object, a little bit of coding using standard gravity and your vehicle would stick to the terrain unless it goes over a ramp and jumps.
I've not used terrain commands for some time so I've forgotten most of the uses. I tend to just load objects for a map and use the collision commands on them.
Warning! May contain Nuts!