My "value according to sound first, looks second" list...
D-303 (great line-out, nice looks, my favorite)
D-311 (good all rounder, slim design)
D-211 (agressive head-out, decent looks)
D-515 (great looks, good all around sound)
D-E900 (great looks, good sound)
D-626 (incredible construction, so-so sound)
D-25S (great looks, "eh" sound when stock)
D-Z555 (nice industrial look, old school digital sound)
D-777 (nice looks & portability, decent sound)
The most I'd pay at the top is $100, and about $50 at the bottom...the players shouldn't be worth as much as they generally sell for. $500+ for a Z555 is beyond ridiculous.