A chain measuring tool is a good $10 investment. If you switch out chains (and clusters) before wear gets above the nag zone, your cranks will last forever.
Given my size I have a feeling I'm going to need to do a lot more than just chain maintenance. I think this is what I'm going to get custom made wheels (deep Vs with 36 spokes), keep extra chains, oil the chain after every ride, and have at least three bikes (a single speed/fixed gear flip-flop hub beater, the Cross Check, and a Long Haul Trucker). Just have to keep extra wheels ready for the inevitable tacoing/wrecking.
