When does one know it's time to upgrade?

Good day members,As the title is open ended and is extremely loaded question, I had to ask to see what others have experienced.
For the reference, I am 30 but have been building 2 channel systems for half my life. Not to mention having ample home theater experience and working as an systems integrator with servers I wouldn't call my sell a beginner when it comes to AV and technology in general.

But what i can't wrap my head around is how anyone has any sense of direction when it comes to pairing equipment.

Current Equipment list:
Speakers: KEF Q350 on KEF S2 stands
AMP : Heed Obelisk SI 3
DAC : Chord Qutest
Turntable : Rega P3 elys 2 M.M. cart & Herbie's Way Excellent II mat
Streamer: Primare NP5 Prisma
SACD : Marantz DV7001
Phono Pre-amp: GoldNote PH10
Rack: SolidSteel S3-4
Power: IsoTek Multiway G2 strip w/ IsoTek Evo3 Premier IEC

Cables: Speaker- Nordost Super Flatline
Interconnects- Nordost Purple Flare RCA's Digital- Nordost Blue Heaven , AQ Toslink
Power- Silnote Poseidon GL IEC

In the past 10 years I've tried these products for 2-channel. PRE-AMPs: NuForce P8s, schiit Freya+ w/ upgrades, Rotel RC1572 . POWER-AMP: Parasound Halo, Hypex Ncore500, Rotel A12 integrated, SOURCE: several SimAudio Moon Dac's and phono pre-amp's. SPEAKERS: Klipsch Rp500, MartainLogan electrostatic's, MartinLogan Motion 60, Definitive Tech SM350& D11, Audioengine a5, B&W 685 M&K75's and KRK Rockit6
I do a lot of research before i buy things and yet most of it has been lack luster (to me)
I dont think my standards are too high because I dont have a specific sound im looking for.

I really enjoy being surprised and wowed by dynamics, sound-stage, separation and weight of the sound.

I am pretty pleased with my system as its for a bedroom listening area that has a space of L15' W14' H10' (Feet)
What i'm worried about is this.... Lets say for example my speakers are the weakest link right now. Yet, i do like the q350's because they were such a surprise (to me). Had good dynamics, created a very good phantom speaker, bass is a bit boomy and a little thin, yet it has personality which helps keep me from being irritated at them. For under $1000 i have been happier with these than most. But, they are a little messy at times, and don't bathe you in sound like some speakers can.

On a philosophy perspective. I dont believe speakers are more important than gear. I do however think, that its critical that one should have some quality speakers that can reveal the quality of gear. But not to the point where they should be 50%+ of my system cost. This is because I have been in a place where i tried building my system around a pair of Martin Logan Motion 60's and it came to a point where I felt like the tail was wagging the dog.

Thanks for reading and any insight/thoughts is good and very welcome.
128x128Ag insider logo xs@2xtk949
I’ve been building and upgrading my system for 50 years. More and more I would reach a plateau where all system components were optimized and balanced and I would just stay there and enjoy the music. Then, I guess I would financially recover and slowly start to realize some change in my tastes or shortcoming in my system. I would then be shooting for a 2x cost upgrade of one component... usually the preamp.. So if my components cost say $1,500 each I would look to go a minimum of double... to get the “wow”. But of course that component was now being held back by all the others... so component by component I would swap until the were complimentary and synergisic. Then I would upgrade interconnects and power. Then enjoy the music for 5 to 10 years... then do it again. My most recent upgrades have by far been the biggest and most profound ever, and most satisfying. But then income usually increases with age.  Since I am retired now I have time to enjoy it also. You can see my system if you click on me.

Equipment pairing is hard. If you get equipment with different weaknesses they can work like filters. The first lacks bass, then passes it along, the second lacks treble, then passes it along, at the end well balanced and lifeless. One of the easiest ways to navigate this as you furiously read reviews from The Absolute Sound and Stereophile, and listen to those components is to listen to famous “house sounds”. All Audio Research, all McIntosh, all Conrad Johnson, all Linn... Naim. When you find the house sound you like ratchet back to the components you can afford. This is infinitely easier and more direct route than mixing this component that won an award with this component that won that award... you can end up with stuff that does not sound that good together. My best friend has a $30K that sounds terrible... I could do better with $5K. He has two bachelors degrees and a masters degree in science... but isn’t good with unstructured problems. He makes good individual choices but can’t figure out how to make them play well together.
It is also easy to make decisions based on the most obvious attributes... treble, bass, balance, micro details and miss the big picture. I will note a components obvious characteristic... but then try and forget about it and just listen, over a couple weeks you get drawn to or not to a sound... not concentrating on it allows your subconscious to get its gestalt. I could write many pages on this topic.

Each cycle was also a learning experience in how to choose components and my tastes. I used to have three test disks I would carry around... I optimized the system around those disks... one was electronic. I didn’t realize until later that I was suboptizing all the other music types. It wasn’t until I got season tickets to the symphony 7th row center that I subconsciously started optimizing for neutral... towards making unamplified acoustical music sound right. That basically improved nearly all others. This was ten years ago, and it had the most profound influence on my system choices. If you only listen to Rock... then it is ok to work to make that sound good. But if you want to optimized all music you need an empirical ruler and large acoustical orchestras are really the only way. Everything else is amplified or not large enough scale to test the ends of the volume and complexity.
Remove the woofer, find the crossover, look for the capacitor, the biggest one if more than one. Hopefully they didn't pot the crossover. You are looking for six numbers with a / between each pair of digits. This is the date you are supposed to upgrade.
If you sit on your wallet, and it is so thick that it causes your spine to shift so as to cause imbalance in hearing, then it is time to upgrade!  ;)