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I have 16"s on both front and rear. If I was to place a 21" on the front and keep the rear at 16", will it change drastically the handling? Will I still be able to tour long distance when the time comes? How much comfort will I lose?
 

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Yup, you will fell a big difference. When I did it on my last bike it gave me the feel that the front kind of "floped" from one side to the other at a stop, but once moving more difficult to notice.
 
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