Hi John,
I'm glad to hear you are considering a BeoSound 2. I have had mine for 5 years, bought from the great dealer in Boston and still use it as my current MP3 player. Only recently I have thought about sending it to B&O for a replacement battery. I have also used the same pair of A8s which came with my BeoSound 2.
I've seen a BeoSound 2, with A8s, a 1GB / 2GB SD card, docking station, BeoPlayer software, original box & manuals, and the B&O leather case sell on eBay UK for £80.00 - £110.00 including delivery. I think this is a fantastic deal and I'm sure BeoSound 2 will become a B&O classic in time. Unlike BeoSound 6, the BeoSound 2 is all B&O and it shows.
The BeoSound 2 and A8 combo is the best sounding MP3 player I have heard. iPods have very poor sound in my opinion, even with the A8s let alone the rubbish earphones Apple provide you with, however I have heard a high bit rate track on an iPod Touch and the new iPod Nano which has been an improvement to my ears.
As for iTunes, I'm not sure whether BeoSound 2 can work with it or not, but I have never tried because I have always found BeoPlayer very simple to use and therefore didn't feel that I needed to try different software to upload my music to BeoSound 2.
For some, it's impossible to have an MP3 player without a screen and I can understand. I wasn't put off by no screen when I bought my BeoSound 2. I saw it as an advantage to its battery life which of course it is, and more importantly now - without a screen, it hasn't dated! I used to ask friends what they thought it was when they saw it for the first time. Now I prefer asking how old do you think it is. The answer is always brand new or no less than a year. So with an undated and stylish design and amongst the best sound you'll get from an MP3 player, I would certainly buy one if I were in your shoes!
There is a disadvantage with BeoSound 2, which is quite a big deal. BeoSound 2 runs on the ancient USB 1.1, instead of USB 2.0 as you will certainly be used to with your iPod. It doesn't take a night and day to upload an album, but it will take about 5 minutes. The largest sized SD card you can use is a 2GB and I wouldn't try using a bigger one because it would then get a little tricky to skip to the album or playlist you're after. I have the B&O brown leather case which has two pouches, one for BeoSound 2 and the other I use to pocket 2 other SD cards.
Yes, yes I love BeoSound 2, so let us (or atleast me) know if you choose to get one! 😐