You might get to that point, but it might take a long time. The differences get more and more subtle as you get up into the stratosphere of flute preferences, abilities, and designs. I’ve played Grinter and Wilkes flutes owned by Kevin Crawford and Jean-Michel Veillon, and while they were clearly great flutes I felt like I’d need a few weeks with them to start grasping their potential (none of those flutes were flutes I’d call “easy to play”), and then I’d probably need a good 20 years of more practicing and learning before I could truly appreciate the qualities that drew those players to those particular flutes.
It’s funny, I tend to be a “grass is always greener” kind of guy in the rest of my life, but somehow I’ve managed to avoid the “searching for the perfect flute” quest. I have a very good flute and I will most likely play that flute for the rest of my life; I’m not tempted to go out and find something better. A good flute is like a good relationship, very complex and sometimes unpredictable, rewarding and frustrating, but as with any good relationship the more time you put into it the more you get out of it.