shit in...shit out
Its all subjective but as someone whos been playing the guitar for over 20 years and has been through a large collection of amps & cabs, i can say the biggest impact on sound 'character' generated for a given set of inputs are...:
- the amplifier
- the speaker
This is the same if its MP3 files, CDs or lossless digital formats.
However like any other process if you put shit in, youll get shit out, lossless or not.
If you cant get a good amp do your ears a favour and buy a pair of Grado headphones - sr60s will do.
Forget your overpriced chavvy gizmo laden B&W, Bose, B&O and Beats etc phones get something that really makes a difference & that says you actually know what youre talking about.