Note that there are likely to be new iPods in November time. If it would really annoy you to buy now and have an old item then, then you should perhaps wait.
I wouldn't though; in the mean time, you can get on with listening to your music.
From what I've seen and heard not all, but most problems are caused by less intellectually gifted owners. As long as you read the instructions, learn how to use iTunes properly and follow the instructions for disconnecting your iPod from the computer after syncing/charging it then you should be fine.
I have an 8GB 2nd generation iPod nano and have had no probs whatsoever. I love mine so I'd say go ahead and get one.
Also, just because you buy an iPod doesn't mean that you have to buy from their online store.
Most legal stores still use DRM on their music. I'd advise you to never buy DRM'd music, whether from iTunes Music Store or anywhere else. Stick to buying CDs for the time being.
iTunes does offer an iTunes Plus feature, which is DRM-less music. 7digital.com also does DRM-free music, and Universal have just announced that they're going to start doing DRM-free music too on various legal music sites.