Sometimes we do not realise we end up chasing more for nothing.
Think about what you have had over the years and assess what you liked and why.
If you are retiring and are looking for you last system I would strongly recommend to find some good audio dealers who will let you demo gear in the shop but more importantly in your home aslo as this is where you will be listening to your gear
Over the years, 30 years I learned to hold onto gear that I really like.
Audio memory is good but side by side comparison is better.
Forget blind testing.
If you have equipment to compare against for the foreseeable future you will know over time if something is different or better..
One example is I kept my laminator dac and meridian CD player. They have never been relegated to storage.
I have had many other dacs Denafrips even the Laiv Dac among others as well as other gear on loan or borrowed.
For me realism in every instrument and voice is first and foremost then detail second. The hifi terms we all know like dynamics separation timing etc are important also but knowing what want first should be your go to place when searching.
You do need to reach a point where you are fine tuning what you like.
Synergy and system matching are not the same thing but both are is so so important.
Room treatment is also a very big deal which includes speaker placement and speaker height in your room.
How loud you listen to your music is another important value.
I like to hear everything a low volumes as well as higher volumes which is difficult to get both right especially without having to make too many adjustments. At Low volumes I sit closer to the speakers but I still want to feel and hear the drums and the pluck notes of the bass guitar along with shimmering smooth highs if they are in the recording.
I aslo realise standard 16bits 44.1 khz is all you really need. Vinyl is also a good source to measure the quality of your digital equipment.
Finally extravagant cables above the average should be sort when you think you are at a point of keeping you system but do get rid of your cheaper good cables that you also like ( again referencing is key)
Note: always use music that you know well when changing or trying out new gear.
I love using Big things going down by Dan Patlansky. His voice and instruments have so much detail. The bass should be there deep and low at low level listening too with note to note distinction without getting in the way of everything else. It gets busy at about 5.25 sec and 8.20 sec this is where separation and dynamics should be controlled without grating your ears.
Good luck in your search