I have been using a Squeezebox for about 6 months, mostly for Internet Radio on my 2nd system. I have found great, commercial-free classical feeds from all over the world. The only problem is that the announcers speak 100 different languages.
I did try a side by side comparison of a hard drive copy of a cd and the cd, using both the toslink and the 75 ohm digital out and the DAC in my CDP. I found the direct cd sound more open and preferred it.
So, to answer your original question, I found the convenience to be not as important as SQ.
This may be because, for me, changing the cd is no big deal, so any lose of SQ was not worth it. Also loading all those CDs takes a lot of time and disc space.
The biggest reason the SqueezeBox did not remain in my main system is that I didn't like the added complication and cables etc. I love the SB and it lives happily on my second system with my turntable and CD changer.
I also tried a TacT 2.2s and liked what it did for the sound. It made a real improvement. In the end I returned it because it was so distracting and complicated my rig.
For me simplicity and ease of use are a big part of convienience and the overall quality of the experiance.