Have $500 for digital upgrade - how should I spend


I have assembled a modest family room system that is geared to social rather than critical listening. I'm less concerned about precise imaging & detail but more into just being able to convey a sense of musicality at various listening positions throughout the room. In terms of musical taste, I very much enjoy blues and jazz. I have $500 left for a digital upgrade to my system which is currently comprised of the following components: Mirage OMD-28 loudspeakers; Wyred SX 500 mono amps; Space Tech QA-001 mk2 6SN7 preamp; Squeezebox classic (no mods); Proceed PDP2 DAC (circa 1991 - Burr Brown PCM-58 chip). Do I upgrade my DAC to Valab, MHDT, etc or the power supply on my squeezebox, or both? Should I update my old no name digital cable?
gotog
Is there anything that you particularly want to change about the way your system sounds?

Why not put the $500 in a drawer and wait until you get some additional cash and go for a more significant upgrade?
Mceljo, I am normally of the mindset to do as you suggest for my main listening setup. But this is a case I am trying to build the best family room system to share with family and friends for a budget of $5000 and don't want to spend much more than that. I have $500 left for a digital upgrade. I am wondering if I spend this $500 on a Valab (or Musical Fidelity) Dac ($200); Black Cat Veloce digital cable ($130) and the rest on upgrading my squeezebox power supply would that be better than say purchasing a PS Audio Digital Link III Dac for the full $500. Or I could go the route of MHDT dac with Black Cat Veloce digital cable and not upgrade power supply on SB. I also have no idea how my existing DAC which was pretty good in the early 1990's stacks up to budget offerings of today.