@Starhalo: I've got an iPod, so I'm familiar with the connector. I haven't been that fond of having to use iTune as the interface to get files on and off of it, with the odd exception of getting photos off of it. I also have a little Sansa Clip mp3 player & radio that acts as a simple USB peripheral and is so much easier to deal with.
To the credit of the iPod and the Sansa Clip, they really don't sound bad when using good headphones. It seems to be better than what I get when using bluetooth to link to my stereo. .. oh... I should mention that I did buy a little bluetooth receiver gadget, which might be the one that you recommended. Kinda handy, but the bluetooth range is limited enough to be problematic in my typical use. The sound is a bit compromised too, at least that's my impression. I've started to just put CD's in my player, which does sound better, and helps justify keeping the CD player around.
As for bluetooth speakers, I recently obtained a Bose BT speaker as a retirement gift. It is the Bose SoundLink mini speaker. For the size, the sound is very good! It looks like it retails for $200, which I wouldn't have spent on it, but that probably say more about me than the speaker. When using it, I'm more likely to use it to listen to a podcast than to music, though.
For me, a lot of the issue is that I'm more likely to listen to an interesting program on NPR (or podcast) than to listen to music. If I'm doing something that requires focus, the NPR program ends up as background noise in much the same way that music would. When I do listen to music, it is often as a background activity. It seems rare that I take the time to just listen to music (and not do anything else at the same time) in the way that I did in my youth.