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I think it is much more of a pain to carry around CDs than to rip them. Once they are ripped, he can store them in an out of the way place. If you get him a Sandisk Clip+(The 2 GB one is only $30) and a 32 GB micro SDHC card($30) then for $60(plus the cost of an earphone or headphone if he doesn't have a decent one) he could carry around something like 300 CDs of music in a device the size of a tiny lighter. Carrying around CDs makes them vulnerable to be scratched. It is much better to keep the CDs as a pristine backup.
I searched for portable CD players. It is hard to find decent ones new, and they are expensive. Imo carrying around a portable CD player in the year 2012 doesn't make sense. I stopped carrying them around in 2005.
"...carrying around a portable CD player in the year 2012 doesn't make sense."
And why it doesn't ? I do carry around a portable cd player and many others do too. Very few people have time to listen to something like 5 plus albums during a day. To carry 2 or 3 CDs in a camera bag around the waist, together with D350, an amp and headphones is enough. [
http://www.walkmancentral.com/products/d-350 ].The sound out of a good vintage portable through line out or an optical line out [ and a portable amplifier ] is great. I do not consider mini or maxi pads or pods as an audio source when I want to hear a good sound.
A bit of a digression to illustrate the point : You might not remember the dumping and trashing of audio medium of vinyl LP and turntables at the onset of the digital era, some 20 years ago. The vinyl and the turntables were seen as dinosaurs being made suddenly extinct by the progress. Now look at what is happening :
http://www.planetofsoundonline.com/articles/yesvinylisback.php Reproduction of a sound wave by 3 formats :
http://electronics.howstuffworks.com/question487.htm
Inconvenient dinosaurs are back. The same can be said of tube amplifiers, some years back many were dismissing obsolete "bulbs". Our ability to hear is of analog nature, our ears and brain do not hear and process the sound in "bits" and in squarish waves and so the vinyl format will remain an ultimate medium for an audiophile purist. That what is natural cannot became obsolete.
Similarly, that what is convenient in the pads/pods format can become annoying and dispiriting. Picking up a lunch menu of songs from 2 or 3 thousand long list of songs can be tedious because it misses the natural joy of listening to an album, the joy of simply putting an album/CD on a tray, closing the lid of a CD player and pushing a play button. I would bet that in the years to come there will be carefully preserved and cherished vintage portable CD players and new DVD players [ with a headphone line out, an audio line out (analog CD type and/or DVD-A type) an optical digital line out ] serving as portable audio platforms for many of those of the audiophile nation. The vinyl medium and the turntables will outlive those that were ready to bury them. The CD and DVD-A players used as sound portables will outlive the ipodniks and ipadniks of today.