There aren't really any 'Dumb' or 'Ignorant' questions about "How much you should spend" on Anything; It's really just a matter of allowing your personal experience level to guide you along with where your comfort level of spending $$$ will take you after you find the answers to what you find puzzling ! Naturally, it's always a good idea to test "the Waters" before taking a flying leap in.
Take all the advice you get from anyone (present company included) with a grain of salt . (Yeah.... I know I'm tiptoeing around making a definitive statement on what to do;but my Brain Cells are still warming up)
I tend to think that the 2 major reasons for hearing 'Noise' from the music we listen to can usually be attributed to 1 (or both) of 2 things ! The first I've mentioned already, that being that it exists in the recording already (That you don't hear it in a lot of modern digital recordings has more to do with 'Digital Compression' than anything else). I'm personally not thrilled about the High Sensitivity rating of most Headphones these days. I haven't done the portable rig listening 'thing' for awhile now (I would only do so if I could strap my Equitech 1.5Q BPT & Metrum Acoustics Hex DAC to my back; That's not happening !). I have absolutely no complaints about any type of 'Noise' ,my complaint is finding the absolutely 'dialed in/Dynamically correct' volume setting from my Amp*. I can get it close,but it's somewhat a PITA to hear what I know exists on most of the recorded music I own. *(Not a Jot; But I'm considering one mostly due to it's low gain capability & the High Sensitivity of my NO; I like these cans a lot hate the stupid Sensitivity)
Hmmm.... after mentioning all this , I personally believe that the amp or DAC that just about anyone happens to be using have very little bearing on the 'Noise' that most people object to. These components aren't creating it ! The noise is in the source signal path. My Equitech BPT can address the below the 'floor' noise that was generated in the recorded signal & became part of what was recorded (because some noise from a mic cable or other random electrical noise) at the time of the recording process) because it is filtering out this 'added' part of the musical signal. DACs & amps aren't able to operate on this type of signal level. I'll repeat myself & say the fault lies mostly on most recorded music (Which for personal 'Philosophical Reasoning' I absolutely refuse to listen to for technical reasons alone .... nevermind my even mentioning what I'm musically interested in listening to; Next to no 'Muse' in too much of what's referred to as Music these days.
I appreciate your insight. I haven't been into this hobby that long but I tend to agree with just about everything you said.
There's really nothing more to do at this point other then to deal with the crappy recordings. You NEVER hear all the background noise listening to speakers like you do under phones.
Good stuff man!