I have a gaggle of vintage units myself, some named and noted for sonic signatures, some like new on stand by for parts, or to unload on some lucky individual with different hearing preferences than me.
Half the fun is experimenting and A/B'g the equipment from a reference point or preferred player, & hosting your own king of the hill contests to compare and monitor differences heard. (I think)
Once you find the sound you like, it is cool comparing other units to this sound relative to the types of music one prefers. (for example d-33 for laid back line out qualities good for classical and makes a great bed-side rig, whereas d-25 punchy more detailed powerful hp out good for transportable rig to bring to work for lunch time, with no amp needed and plays great at low levels where the lack of bass or thin qualities mixed with the non constrained highs do not become overbearing because the listening volume is at minimum. But if the d-25 was your main gun the sound is fatiguing over time 'note stock d-25 not modded')
HiFi equipment in any genre or age is collectable regardless of state, as the electrical engineering and innovative designs were impressive for these units and are physically noted from the build quality alone.
I own a very new Sony MP3 weather CD player does it all type of unit. I use it when I do things around the house, the sound sucks. It sounds like you're listening to the flat tunes through a beach of sand and is not clear. As others have mentioned the headphone output is puny and must be turned to 8/10 in a QUIET environment even for Grados...not to mention that the original d-303 I have from the 90's is still in perfect working order; however, I can think of over 20 (literally) PCDP's I have purchased and that which has broken thus since that time. So you figure it out, buy a crappy new portable unit that feels about as sturdy as the toys you purchased from safeway toy isle, or take a chance with an older unit where sound/sonics matter.
Those new units are great if you're listening to your cans always on the move, on a train, or in a noisy env where detail and sonics are masked/lost any who.
And from a home units perspective, there are caveats there too...because people find the same "detail oriented" problems or tweaks wrong with these units too, but the dangerous part is there are no reviews or knowledge bases on these units, so you stand to lose 300-500$ instead of 30$-200$...
Plus note that the really sweet units all sold for over $300 when new, and must be taken into consideration, as that is like 10 x's today's cost of an average unit (we will call it $30 for the current sony "sandpaper spinner 2000"
...well if the d-303,d-555,d-25,d-15,d-777, or d-515 was on sale today at BB it could potentially be worth $3000 per unit for one of these bad boys in todays profit/cost ratio..
The rebuttal is cost per mfg, and additional features VS total cost of ownership, and that is exactly why people despise the new units because they do not sound as good,and are not as catering to line-out amps and such.
I have owned a Cambridge D300SE (now Broken) and an older Marantz unit (that always skipped, even after it was serviced, embarrassing and could not even sell it)
so can not help you out there, spent bunches of cashola on those two transports alone (can you say close to enough to float a new pair of PS1's??)
So it is completely up to the ear of the listener...I find listening to music most enjoyable when one player does not spin a cd well for sound, and I can easily swap out and switch to another that does. Very cool stuff.
PS.the PCDP also makes cool looking home rigs when paired with hp amp,tube amp, or any other combo of components...everything all compact like!! the metal design and backlit display is just the gravy!!