The main source of resistance on most trainers (including your Kurt) comes from wheel speed, not from roller pressure. So I tighten the knob just enough so the tire slips only a few times during the workout (I expect it to slip only at very high torque moments, like the first few pedal strokes of a sprint).
Simulating hills on a trainer can be difficult since often cadence drops when standing. So I shift into a higher gear to speed up the wheel, and thus increase the resistance in the trainer.
You can see how the resistance in your Kurt Kinetic trainer increasing with wheel speed here:
http://www.geocities.com/almost_fast/trainerpower/
Scroll down to see your individual trainer.