I've had two Clips develop terminal headphone jack issues within nine months of very gentle use.
And, let me tell you, using right angle plugs does NOT prevent the issue : my Clips were used with a right-angle plugged HD 25-II.
I should also add that I have never wrapped my headphones' cable around anything, least of all a Clip.
To my eyes, the Clip's headphone jack dies for a single, simple reason : it's not made to last. The Clip is cheap because it's a disposable player.
As it happens, I'm not saying that this is a bad equation, or that buying a Clip is a bad idea. Putting 40 euros every couple of years into such a capable player (the Clip has a two year warranty where I live) is by no means a bad deal. Just don't expect the thing to outlive its warranty.
I have been using Sandisk Clips for over 5 years. I had only one break, and the only thing that broke was the clip.