1) Good choice on the iPod. You wont be dissapointed with it.
2) Ignore any ppl that post links to the "battery problem" In 99% of cases, the battery will last for years and years.
3) iPod are fine for sport usage. But i`d reccommend a 3rd party case for it, such as the DLO Action Jacket.
4) The iPod doesnt skip. It loads 32mb of songs into some solid state ram that it has, and powers the HD down till it needs it again, which means no skipping. At all.
5) As for damage whilst running/jogging. Dont worry about it. I go running with mine, and its fine. If you need more than one opinion on the matter, then visit
iPod Lounge Forums, and ask there, you`ll get the same answer off everyone there that ive given.