If you're prone to overthinking stuff, the tone quest can easily become a bottomless rabbit hole that swallows so much time and $$ that your actual music (and possibly bank balance) suffer. Don't do that "-) Marcus Miller once wisely said something along the lines of (paraphrased).... gear is important, but get it figured out reasonably quickly and get on with actually playing. No matter what your rig currently is, there's always new glittering stuff out there imploring you to keep your gear carousel spinning.
I love tweaking my gear, and admittedly waste a lot of time and $$ doing so. I am well aware that I do it for its' own sake/ enjoyment, and that I sound best/ suck less when spending as much time making music as I can (which is never enough).