I also prefer to actually
purchase in lossless format as it seems a rip-off to do otherwise, (by that I mean I purchase the CD's and rip them.)
However, to rip the CD's in Lossless format is a waste of time if you already have the CD. You are not getting any higher quality sound and you are increasing your storage requirements dramatically. A single run-of-the-mill song in Apple Lossless can be 30 Megs or so, the same song in high quality AAC might be less than 5 Megs.
This means that you have to carry around some gigantic brick of a music player to even have a reasonable selection of music at your fingertips. Needless to say this detracts from the entire concept of a portable digital music player.
It's been proven again and again that the average ear cannot tell the difference between an *mp.3 and the original file and that even audiophiles have a hard time if the bit rate is high enough. With AAC, I don't believe there has ever been
anyone who has reliably been able to tell the difference between the original and a 256 AAC copy.
If you are ripping music to Lossless and carrying it around, all you are doing is wasting space on your player. Keep the CD's on the shelf at home for safekeeping and rip into AAC and you can't go wrong.