I recommend the Panasonic SL-SX460 (under $100) along with a good set of headphones.
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I think it is a BAD investment! Those "things" are cheaply built, and overpriced! And i don't think, their sound is even acceptable! I've checked few (Panasonic, Sony, Aiwa...and Optimus! And believe or not, Radio Shack's Optimus, felt "right" and sounded as good as the pricier Sony discman or Panasonic!! If anybody, has discovered any better...please? I am all ears!
The old Optimus CD-3400 used to stir up controversey over it being as a good sounding transport compared to the likes of Levinson. Stereophile had mentioned it quite a few times, even seperate power supplies were sold for them. I also like the older Sony D-555 more so without a DAC than the CD-3400. The CD-3400 has a mini jack to RCA, and the D-555 has a toslink digital output. I would look for a model with a digital output if possible.
I would check the Headroom web site as they usually track which is the best sounding portable cd player available. My experience is that most portable cd players do not sound very good. I own two Radio Shack CD3400's and use them occaisionally with either Grado SR80 or Koss Porta Pro Headphones. I have found that the Radio Shack sounds better plugged into my NAD receiver and then using the headphone output on the NAD. There was a time when the line output from the Radio Shack was competive with many full sized, budget cd players, but I think that time has passed. I also use the Radio Shack's as cd transports in my second system and they worked fine, as long as you use the right cables (do not use Radio Shack cables) and a jitter reduction device. You certainly cannot find anything cheaper to use as a transport and I have compared this combination to three higher priced and highly regarded cd transports and one cheap cd player with a digital output and stayed with my Radio Shacks. I recently tried to have one of the Radio Shack's serviced as the digital output jack is wearing out. Radio Shack would not fix it, saying it was too old.