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.
128x128tk949
I like starting with the speakers first.  I like to test them with acoustic music such as jazz, symphonic and vocals.  Especially important is piano and strings.  I usually disregard specs and just use my ears,  if they past this test, they will usually sound fine with amplified music.  Match the electronics to the speakers.  The one specification I do look at is the impedance curve of the speakers and make sure the electronics will be a good fit.  I have found having a tube pre amp and solid state amplifier can be the best of both worlds.  An integrated with a few watts in class A before it transitions to class A/B also is effective.  Enjoy the journey,
Stay off forums.

Listen to your existing system, and no other. You'll never experience upgrade fever.
There is lots of good advice here already. I will add that you might consider identifying some potential upgrades for various parts of your system, then shopping from that list when you have the benefit of unexpected funds, such as an inheritance, annual bonus. or winnings from gambling (although you probably can’t afford both that hobby and audio at the same time). If you have a list of potential components, you may then buy the one that you can afford and that is available at the right time at the right price. If you are fortunate, you can resell what you don’t like without losing much, assuming that you choose components that are in demand. Timing is a key variable in the market for used equipment, and you also never know when a dealer may have a perfectly good open box or demo item for sale at a good price.