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My program uses around 20 jars (for a total size of about 30mb). For now, they are all added to the classpath for the released version, and all jars are deployed with the rest.
Would there be a performance impact if I was unpacking them and repacking them into one jar?
No, but there would not be any advantages either.
Personally I think you should deploy the very same jars that you develop on, unless you have a good reason not to. Repackaging can lead to subtle issues, if the original jars were sealed, but for an experienced team who likes an occasional challenge these are easily handled.