I have played around with the Squeezebox (all of them SB1, SB2 and SB3) extensively. The stock SB2 or 3 using analog out is surprisingly good, perhaps stonkingly good given the price, but not high-end. The stock SB2 or 3 using digital out can reach high-end quality but depends on the DAC, and can be bettered by a good (read kilobuck) transport. The difference however IMO is totally outweighed by the greater ability to listen to what you want to listen to. If its about the music, then I wouldn't trade the SB convenience for the slightly better sound of a good transport. You don't have to get the SB modded expensively to raise the bar to match a good transport though. Get a good linear power supply, stuff a couple of Black Gates in the SB2 and you have a really excellent digital source. You just need one Black Gate as a bypass cap on the DC input and another to replace the so-called 'big-ass' cap. You can go further and put a transformer output in but that may tax a few people. IMO this takes the SB2 to a level where it is very hard to develop a reason to buy a high-end transport. The SB3 is a little tougher because it is harder to stuff things inside the smaller box. Getting the Bolder or Red Rose Mods done improves things further, but not a lot in terms of digital out. The analog improvements wrought by these mods can mainly be achieved with 10 minutes of soldering and a couple of Auricaps. But with these mods you don't have to get out a soldering iron, just your check book, and you have something easier to sell when something better turns up. I have gone the route of doing my own mods and the SB2 competes favourably with the likes of the Meridian 500 and the TEAC T1 in my system (Currently Prima DAC, Nuforce Ref9.02 and Verity Fidelio, connected by Jena). I wouldn't think of going back to getting a CDP.