I would avoid pushing a bicycle with a flat for a long distance due to causing improper wear on the tire and the rim.
Also, when flatting, your bicycle is useless until it is fixed? Right? So, the repair will have to be done eventually. In my book, better sooner than later.
I used to be really slow and clumsy at changing tires. Especially Gatorskins, once you install these tight bad-boys on your rims you understandably don't want to have/fix a flat. So, as I have changed a tires a few more times having more than one bike I have gotten better. At least enough to have the confidence to fix one on the roadside. Some tire tools I have used have been too bulky for a skintight tire like the Gatorskins and have found thinner ones. Belief it or not, reinflating the tire after fixing the flat is the most daunting task to me as there are only a couple of good frame pumps and those can work you to death for high psi tire.
I'd say get a clear picture of exactly what you need to fix a flat on the roadside. The repair materials are not that many (as someone mentioned a wedgepack is a great for these items.) It's just battling the Gatorskins that can be a difficulty. After the Gatorskins have been ridden on for awhile they become easier to manipulate to reinstall on the rim.
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Last edited by georgiaboy; 05-31-08 at 06:18 PM.