I looove the steep stuff. Steeper the better. I take vacations from flat Texas to hilly places and seek out the big steep hills.
Gearing. Comes in handy. 39x23 won't help you much on a sustained steep grade.
39x29, better. I can get up just about anything with that, if it's dry / paved and I'm not suffering from empty legs.
In the rain, after 200k+? NFW... bring me a triple and one of those giant bailout cassettes.