I find music streamed through a Squeezebox SB3 from Apple Lossless, and Pandora.com files to be smooth and cheap.
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Well what I've done as a temporary solution is install Rockbox on my 5th gen iPod and set the treble cutoff frequency around 14,500 Hz. This actually makes listening bearable, but does seem to cut out a lot in the upper range. I'm willing to live with that if it gets me cheap digital playback that I can actually listen to without making my ears bleed. I may try the DIY mod that is similar to the Red Wine Audio iMod.
Stereophile did a recent review of the Sony Playstation 1, and the reviewer said he couldnt understand what all the fuss was about with the Sony he had been reading about on the web.
I'd get a Bolder modded Art DI/O DAC for ~$350 and try it with both players,then use the player that sounds best as a transport.
If you want cheap, then you will sacrifice detail. Most cheap solutions eliminate harshness and fatigue by rolling-off or compressing the highs. This also tends to compress the dynamics a bit. If you dont care about sacrificing some detail or dynamics, then go for it.
Poor AC-coupling caps are the first thing that goes cheap, and this will compress and roll-off. DC-coupled DAC's are more expensive. Power subsystem is the second thing that goes cheap, with similar effects and a big impact on dynamics.