I'm a farily serious iPod user....I bought a 1st Gen two weeks after they were announced way back in 2001, and I've used an iPod 5+ days a week ever since. I currently have a 6G "iPod Classic" (the current main-line iPod) that I'm listening to right now...and we also have a 4G iPod and a 2G Shuffle "clip" at home.
As for iPod accessories, we have two different "iHome" clock radios, and also some off-brand of iPod jambox (don't remember the brand right now) that we carry outside to the Pool.
Honestly, I'm not entirely sure I'd really use one of those things because (A) I don't imagine the sound quality would be worth a damn, and (B) it's only somewhat waterproof, which means I'm not going to float around in the pool with it....so if it's just gonna sit on the side of the pool, I might as well use my current iPod jambox.
But then again, $100 shipped is such a good damn price, I just might have to order one anyways. LOL