will headphone jack connection wear out?

The USB cord would be the reason I wouldn’t have a permanent plug in mine.  Plus my docking station (which I use to charge it at home because my old, old, old laptop won’t charge it) wouldn’t support it, there’s no room for it.

I unplug it to add music,moves, etc., to it at work using the usb cord, unplug it to use the cassette adaptor in the car and unplug it to use my docking station at home.  I’ve even used 4 different headphones in it (original which I don’t have anymore, some I had at work, some $20 ones that aren’t long enough to go around the back of my neck and $5 ones which I use all the time now [long enough cord] ).

So far no problems.