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I Love PAIN
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I am currently limited to 7 on the back being that I ride an older steelie. I upgraded the right shifter from the down tube to STI. I can upgrade the left shifter to either a double or triple crank. Is it worth upgrading to a triple to get the extra gearing. I know I'll probably have to upgrade my derailers, but this bike fits me like a glove and I want to keep her around for a while. Any helpful input would be appreciated.
 

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If you decide to go with a triple you will also need a new crankset as well, so that will be an additional expense. Whether it is worth it depends on your fitness level relative to the terrain you are riding. Big hills and low fitness equates to needing lower gears hence triple. If flat and great fitness may not need the extra gearing. If unsure, now might be a good time to do it, if done later will need crankset and shifter anyway.
 

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Get me to In&Out
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I agree with Carver. It is about what your needs are. A triple in the front will give you much friendlier climbing gears if you need them. Be honest with yourself about it and base it on that. Another option if you need easier climbing gears and want to keep a double up front would be switching to a compact crank. It will give you similar gearing, though it won't give the much cherished "granny" gear when you really need a break.
 

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As others have said, it depends on your strength, fitness and riding style, and, very importantly, the terrain on which you ride. You can give yourself a test. Find the steepest hill you expect to (or want to) ride, and ride up it in the lowest gear you have now. Can you make it? If so, are you reasonably comfortable, or struggling horribly, and really in need of a lower gear? Do you feel like your fitness will improve enough to make the current gearing acceptable? If you decide it's low enough, you're good.

If you do want a lower low, can you get it with a wider-range freewheel? If so, would the wider gaps in that freewheel be a problem you'd rather not live with? If so, you may want the triple.
 
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