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?

ezstreams

Thank you both for your insights and suggestions. My understanding is that one of the major headphone shortcomings is their lack of a “realistic” soundstage.  That and comfort issues in long listening sessions. The organically accurate sound i described is far more important to me than sound stage. That’s my personal preference. I get frustrated with my system whenever i recognize that I’m not hearing those details. It’s never bothered me and I’ve never had the urge to turn my system off when i couldn’t place the drummer, guitar, piano, or bass location on stage. Long term listening session head and ear fatigue could become an issue. 
That said, one reason I’m even considering headphones is nobody else in my family (wife, son, daughter, their spouses, or any of my 5 grandchildren are interested in hi-fi so its really just me. 
@inna with my upcoming retirement, im considering getting out of tubes (at least on the power side). Do you have any experience wth the relatively new Primaluna EVO 300 Hybrid Integrated amp?  Thats a non-headphone option im considering. The other option i find intersting, is even more of a departure from my current system, and that is to go full solid state with something like the Hi-Fi Rose RS 520 streaming integrated. 
I need to research if there is a way to listen to these options without having to buy them all then resell what doesn't provide what I'm striving for.  Here is where the insights and opinions of the Audiogon members is so valuable. 
@yyzsantabarbara I’ve read great reviews on the RAAL ear speakers. How do you find them for extended listening sessions from a comfort perspective?  My current Primaluna integrated has a highly rated headphone amp. 

ezstreams, I can't advise on the equipment, I only try to follow more expensive pieces and mostly tube equipment.

I personally don't enjoy headphones because I don't like music in my head as opposed to the space in front of and around me, but I know that some really prefer headphones actually for similar reason ! Yeah, in any case, headphones must be comfortable. 

 

I have that exact sound you are looking for. Jazz (and everything!) sounds amazing. Inner detail, perfect timbre, instant attack, black backgrounds, explicit detail without fatigue, sweet as a nut.

Original recordings on vinyl. Idler drive. Decca cartridges, tubes, Quad ESL.

Having just flunked my audiology test, one advantage of headphones is that 

some of the newer ones offer DSP in that an App runs a hearing test and then sculpts the sound according to one’s needs.  I am not a big lover of cans but this might make some sense for me to investigate 

As you seem to like what you have, I would recommend trying some “better” cables from the cable company.  In my experience, the difference between cables can range anywhere from no difference to “holy sh%t” and the only way to tell is to try. I would try speaker cables first, although many say power cords. Looking for that last 10% can be time consuming and expensive.