I (and others I've talked to) feel that nothing has improved as dramatically as digital gear in the last few years. Newer generation players sound much better than those of just a few years ago. Speakers are slightly better - some designs that are 10 years ago are still current models (e.g. Thiel 3.6), and amps have been tweeked (Mark II becomes Mark III) which sound different but maybe not better.
So I guess it comes down to you, do want the best possible sound or do you want a trade study of dollars vs. performance. I will make one recommendation - audition the GamuT CD player, it sounds wonderful. I did an A/B using the GamuT and its internal DACs vs. GamuT and an external Audio Note $33K unit and the GamuT by itself blew the Audio Note away - no contest at all. Like yourself I've thought of buying a used high end CD player too but not anymore. Oh and try the GamuT amps as well - very very smoothe SS with incredible dynamics.
So I guess it comes down to you, do want the best possible sound or do you want a trade study of dollars vs. performance. I will make one recommendation - audition the GamuT CD player, it sounds wonderful. I did an A/B using the GamuT and its internal DACs vs. GamuT and an external Audio Note $33K unit and the GamuT by itself blew the Audio Note away - no contest at all. Like yourself I've thought of buying a used high end CD player too but not anymore. Oh and try the GamuT amps as well - very very smoothe SS with incredible dynamics.