A part of the problem is that jack shafts tend to very slightly in width. If you use a cable that is slightly bigger it can cause problems when you go back to normal sized cables. They are also just inherently more susceptible to wear and tear. Even high quality jacks like the Switchcrafts that I used to have in my G&L bass go bad. When it happened to me a second time, I replaced it with an open frame jack mounted on a Les Paul jack plate.
Before you have finish on the guitar seems like a good time to drill out the hole so that it will accept a standard open frame jack. This is relatively easy to do with a step drill bit like this:
Once you have the hole the proper size you can use an open frame jack one of the new Telecaster style jack plates, a "Les Paul" style or a a "football" style jack plate.
Not as elegant s the barrel jack, maybe, but more durable. Also much easier to do before the electronics are installed than after.
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