I will respectfully disagree with this. Somebody who says otherwise is not a hypocrite but an inexperienced musician. Yes, some will jump at the opportunity but those who don't are not hypocrite, they just know what they need to get the job done. What you look for in gear is character and how it translate to your music, how it sits in a track. Sometimes that character comes from old, cheap gear and sometimes it comes from really expensive ones. It all depends on the type of music you're creating. Would RATM's debut album be more influential if Tom used an orig 59 LP and a Dumble amp? Would Eric Johnson be able to create Ah Via Musicom w/ a first act guitar and a pignose amp? Would Marley's Redemption Song be more beautiful if he used a 20k acoustic? There is no measuring stick in art.
of course it goes without saying that when you upgrade, you will get the ones that are better suited to your taste. it's simple common sense. getting better gear doesn't simply mean getting the more expensive stuff out there. you still have to be in-line with your music. if you are a hardcore strat guy and you currently have a cheapo strat, your goal may be getting a better Japanese or American strat. why would you "upgrade" to an LP unless you want a different flavor? when a sniper upgrades, he upgrades with a better sniper rifle with more advanced scope or whatever. he won't "upgrade" to a bigger machine gun or something.
the scenarios you cited are all what-if's. no way to prove or disprove. some would argue that RATM will still sound the same in a Dumble and Eric Johnson can still kill a song with a small amp. point is, you wouldn't know what will happen if those scenarios actually happened.
Imagine if all forum members here own boutique equipment. High end guitars, amps, efx, the works. Do you think we would all get along by then? No! Because it is human nature to look for the greener pasture, to look for something better than the next guy. I'm sure there will be somebody who will buy the more expensive gear, brag about it and say "look, my stuff is better than yours" but there will also be some people that will say "what I have right now is enough for what I want to accomplish, now excuse me while I make some music".
of course we still won't get along - that's where the subjectivity comes in! only the inexperienced will buy more expensive gear to brag. those people are laughable.
those that stick with their gear and don't upgrade may say that they are contented. but how many are REALLY contented? i daresay that majority have other priorities in life which demand a bigger chunk of their budget than making music. it can be another hobby, family matters, what have you. that is respectable because they know their priorities. but only a small percentage of those people can actually claim that they are contented in the true sense of the word.
i still maintain the position that a truly experienced musician - when given the opportunity - will upgrade his gear to better and more expensive ones that he thinks will improve his music-making prowess.
