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’m surprised that no one mentioned speaker placement and room treatments.  I know those are my weak spots due to the limitations of my listening room.  Other members have noted their experiments with changing speaker placement and that even small changes in location and toe-in/toe-out can have significant effects.  Then there is the application of room treatments/panels and bass traps that can make a real difference in the sound (I’m told)..

I am impressed that a young man of 30 has already sampled so much equipment — more than I will in my lifetime.  Impressive. I haven’t checked your profile yet, but I hope you post photos so we can see your evolving system.  Good luck in your quest. 👍🏻
+1 - test system/speakers with well recorded acoustic music, symphonic, chamber, solo piano ect. If you get that right, everything else will be right as well. Solo piano is very hard for a system to get right. Unless of course you don’t like or listen to that type of music. I figure how do I really know what a rock band should sound like? If you hear a rock band live, it's way different from the same band in the recording studio. But by going to the symphony and other acoustic concerts, I’ve developed a sense of what sounds right.

Consider a DIY project- I’ve learned a lot about speakers by building my own over the years - what sounds good and what doesn’t. I’ve probably built a dozen pairs over the decades, and it has really helped me ID what I want in a speaker’s performance. Room treatment can make a big difference especially in a lively sounding room, when you get the reflected sound under control.

Over the years, I’ve found that I prefer high sensitivity speakers and tube amps and I listen at lower levels than I used to. A good R2R DAC made a big difference for me as well.
I you're satisfied with your system and its sound then you don't have to change anything.

If you feel you want something new you will have to try different things like different brands or types of speakers or amps and see if something suits you. This may not cost much more than your current parts but if you for example go from box speakers to horn you may have to change your amp too.

If you want clearly better sound you may have to change many or all parts of your system. My thinking is that you can start with for example speakers but should budget for something that costs 50%  to 100% more than the ones you have to get a clear improvement. I personally just changed my amp to a much better one and it really lifted the sound. I could not afford to buy a complete new system at this level but if you have that budget then just knock yourself out. It looks like your speakers are below your amp so new speakers may be a good idea.