If headphone jack problems are a worry, I'd be careful about the zen xtra. It's got a big problem there. check the nomadness.net forum, and search for headphonejack problems.

I hope it 'comes together' for you also Austonia. But sometimes new technology - which moves so fast these days- can bamboozle 'older' folks.... folks more set in their ways and slower than they once were. Sometimes you just have to move aside (when you can no longer keep up) and let the new...

it's a known issue. i had it; and so have many others. go to nomadness.net and go to the zen forum and seach on 'background noise' or background hiss' and you'll find a lot of issues.