Like anything else on the internet, it's hard to gauge how big a problem something really is. Kimber external extractors seem to have more problems than internal extractors, judging by internet feedback. I and many others have seen many external extractor guns not function, more so than internal extractors.
Improper extractor tension is the leading cause of failures to feed in out of the box 1911s, in my opinion. This can happen with internal or external extractors, but it seems to happen more with external extractors, at least when we're talking Kimbers. S&W, Dan Wesson, and Sig don't seem to have the number of problem guns with external extractors Kimber does.
Someone who I respect offered the opinion that Kimber's external extractor design is too short. This means less leverage, leaving it more succeptible to the inevitable variances in spring tension that will be present in Kimber's extractor springs.
The biggest reason you see people bash the external extractor Kimbers is that with an internal extractor, if tension is incorrect, it's easy to fix, while with an external extractor Kimber, it will require a trip back to the factory. The same could be said of other manufacturers of external extractor 1911s, but they don't seem to have the incidence of problems that Kimbers do.
There was an informal reliability survey we did on the Kimber forum of this site. Though the number of people that participated was small, the last figures I tallied were 92.68% of internal extractor Kimbers that were reliable, and 55.56% of external guns that were reliable, of the ones that various people owned or own. It's a small polling pool, with only 34 people participating as of 2/5/06, but there is a definite trend here.
The bottom line is shoot your Kimber, and if it works, don't worry about it. Kimber recommends a 500 round break in, I believe. If it is reliable in the next 500 rounds, then you're probably good to go, and I would not worry about it getting worse, as extractor tension will only lighten up, and the problem is too much tension most of the time.