From my experience, getting problems with earphones plug is often a reason for dicarding an ageing port.
To prevent this (or make it happen later at least), one might :
... never (or as rarely as possiblle) unplug the jack.
or
... plug an extension cable permanently so that the cable will be replaced over time, instead of the player.
Sandisk Sansa Clips's clip is quite useful for that :

For the record, I use a Koss-VC20 cable which has a remote volume control at the other end, is cheap and strong enough... for me. The blue string is used to hang the remote while moving...