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.