When you see a better one for a really good price?
Generally, you just replace the parts of the crankset as the wear out. Chances are the bottom bracket will go first (unless you only ever ride in perfect weather) - usually there are squeaky noises and wobbly feelings giving you a clue here. Then you might wear the teeth of one or more of the chain rings to the point where replacement is a good idea. The crankarms themselves very seldom wear out, even if they can get pretty scruffy looking as the paint/anodizing wear off.
When I replaced the crankset on my mountain bike, it was because I had been chewing through isis bottom brackets at an alarming rate (like, less than three months) in the British winter and wanted to try a different system to see if it would be more durable.



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