For what it's worth:

I have a bedroom system which consists of a Squeezebox Classic with the
digital outputs going into a Headroom Desktop Amp which has a built-in
DAC installed. I use it with several different headphones: a Sennheiser
HD650, an AKG K701 and an Ultrasone Proline 750. All three sound great
in this setup and using the SB3 gives me instant access to my music
library without having to deal with any CDs. In fact, this system
doesn't even have a CD player in it.

Most full size headphones really benefit from the use of a dedicated
headphone amp since the headphone amp in many devices, such as the
Squeezebox Classic and the iPod, is usually not made to drive larger
headphones and is therefore somewhat under powered.

I think many of the suggestions given so far are very good and offer
you many very good choices and several possible ways to proceed. Adding
an external DAC to the SB3 should make for a big improvement and then
adding a dedicated headphone amp will yield even more improvement.
Whichever way you finally decide to go I think that you will be
pleasantly surprized and very happy.


-- 
ralphpnj

Lock, Stock and Two Smoking Barrels -> Snatch -> The Transporter ->
Transporter 2

'Last.fm' (http://www.last.fm/user/jazzfann/)
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