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Depends how hard the bunch is going, or what kind of cadence you enjoy. Do-able on the big ring and may be worthwhile because the bunch often kicks at the bottom and top of the hill and you don't really want to be fucking about changing gear on the front.
Yes, I've dropped a chain going over the top before.
croft
How much climbing in a cat 4 crit at hog hill?
Is it a small chain ring job even if running a compact?