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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
fuzztone's avatar
fuzztone
5,510 posts
 
When the scratching stick doesn’t reach the itch anymore.
ORThe crossover was potted.
tk949's avatar
tk949 OP
4 posts
 
@audiomaze That isnt me in the photo :p Just thought it was pretty fitting posture for an audio forum.
I sit in a low back silk and down filled upholstered chair. I actually find leather to be a little too reflective. I also prefer to have a chair with an internal structure made of wood for listening in.
sheridanmartinj
50 posts
 
As Samadhana so stated when you start listening to your system less and less more than likely its time to upgrade.  I personally start my up grade every 5 to 7 years with a better Preamp next speakers which I don`t think I`ll be upgrading my Maggie 3.6`s anytime soon I`ve own for 6 years in conclusion  my cartridge which in IMHO is the right route for me to improve a system
ecscott482's avatar
ecscott482
44 posts
 
I have several music systems, living room, shower, garage, boat, car etc. I spend most of my time enjoying music and not upgrading.

Maybe, in the winter, I might get bored and get a new set of tubes for my amp, but now, it is time to go outside and enjoy the spring weather.
rmdmoore
151 posts
 
As someone who has been building systems for 20 plus years my experience is that while the components are absolutely extremely important, in terms of sound characteristics, nothing is going to make a difference more than a speaker. I've always auditioned multiple pairs of speakers at a number of different retail locations before buying a pair. Once I know what speakers I want I them start working through which electronics I want to push them. This is where it's important to have more than one retailer that has your speakers because you may want to try 2 or 3 sets of electronics at each place. Last part is source. It's extremely difficult to know what to expect from a source unless you have an idea of what the system is going to sound like and how revealing it's going to be. 

To me, it seems you have some quality components and, though somewhat satisfied, feel your speakers are the weak link. I think your probably right. Based on the other components you have I'd look in the 2-3 range and keep a really open mind. Go listen to a lot of speakers. 
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