Yes, another audiophile at a crossroads story and request for advice

I find as I’m rapidly approaching retirement that 2 competing thoughts about enjoying music after i retire. First, Im really looking forward to having the time to relax and listen to music any day of the week (not just the weekend now). Second, I don’t expect to be continue any significant investment in equipment upgrades post bringing home a paycheck. 
My current system consists of a 30+ year old Linn LP12 with Linn cartridge and Vincent PHO-701 tube phono pre-amp. I only listen to analog when i want to enjoy an album i bought in the 60’s - 80’s. 
90+% of my listening is streaming Tidal using Roon via Roon Nucleus, Lumin D2 as a streamer only, feeding a RME ADI-2-FS DAC. 
i still enjoy my CD collection (9% of my listening) and still purchase CDs) on a Primaluna tube CD player. 
All these are connected to a Primaluna Dialogue Premium HP integrated amp with original primaluna tubes from Upscale Audio.  My speakers are the original Joseph Audio Perspectives (not the graphene version). 
Power and interconnect cables are mid-level grade and power management via Niagara 1200. 
i listen mostly to instrumental jazz. 
This system is enjoyable, but I’m missing the last elements of sound details that reproduce an accurate organic sense of hearing guitar strings being plucked or picked, drum sticks hitting/tapping membranes or brass cymbals, the sound of a string base wood cavity vibrate. Hopefully that describes what im looking for. I do not like hyper/etched detail especially in the upper frequencies. 
I will add that the Primaluna CD player is the most enjoyable source of the 3 I currently.  Oh, and i also want to simplify my system. 
So, if you come with me this far to the intersection, heres what im debating. Should i chunk the integrated and Perspectives and invest in a top notch set of headphones (like the Focal Clear MG) and dedicated headphone amp?  In other words go to a headphone system. Or should i go the route of chucking all but the Perspectives and the Nucleus and invest in a high quality Roon approved integrated amp with built in DAC/Streamer?