I rip my CD's using Windows Media Player 10. The ripping format is WMA lossless. I just insert the CD and let WMP rip away. I did buy a high quality CD drive and I set my rip speed to 2X. I played around with EAC and foobar but found them too much of a pain in the Butt. I compared rips from EAC and WMP and I was hard pressed to hear a difference. And, when I did hear a difference it would be very subtle. I guess this is where EAC's superior ripping was making its self known. Occasionally, WMP 10 has a problem ripping a certain track, so I clean the CD and re-rip. This has cured the problem every time so far. So, if you want the ultimate rip, then go with EAC. I am happy with giving up 2-3% for the ease of use of WMP 10. In addition, WMP 10 labels all the tracks for me. Its very rare that I have to edit them. And, when you have 1000s of CDs, you can see where this becomes an issue.
As far as playing back classical or jazz CD's on the Squeezebox, there is no break in the music as long as you play the entire CD. Now, if you add a few tracks from a classical CD to a play list there will be a very slight gap between the tracks. I don't use play lists so I don't have a problem with this.
Why did I choose Bolder over Redwine? I spoke to both Wayne and Vinnie before making my decision. They both offer great mods and great customer service. And, they are both very knowledgeable and polite on the phone. It was a tough choice but the deciding factor was that the Redwine mod uses a battery supply. I have s sleep disorder that requires me to sleep with the TV or stereo on. I sleep 16-20 hours a day. So, this would mean about 2-3 battery changes a year on the Redwine mod. I just did not want to be bothered with battery changes.