...So back to your question, I'm a tone guy when it comes to producing sound but maybe less so when it comes to reproducing it. Ha! I've worked in studios most of my life and gotten used to making do with whatever the headphones might sound like. As long as I can hear what I need to hear to play with the band I can deal with it. ...
I've just been lurking on Rusty's thread here, mostly because I haven't any experience at all with IEM's, and therefore nothing to add. It was strictly for educational purposes, in case I ever did. But then this snippet of Jimmy J's reply just tied my brain in a square knot. Pretty much equates to "Use The Force, Luke..." 
I need to be more disciplined, especially in the studio, but onstage too. Trust the bass, trust the engineer. Going to go write that 100 times now...
Great thread guys. 
Likewise, I've been lurking in hopes of picking up some things for when I get IEMs (I'll have to show Jimmy how to grimace so fiercely those babies will pop across the stage. Maybe the whole band can do it during "Your Smiling Face"). Oops, I digre
Anyway, your comment about trusting the engineer(s) brought to mind a nifty technique I discovered by accident back when I was playing with Roomful of Blues in the 80s, and it's never let me down. We had a gig at the Hatch Shell in Boston with a couple of other bands and everybody was complaining about the soundmen. It sounded fine to me (especially for an outdoor venue with thousand of spectators), so I wandered over to the board during the opening acts and struck up a conversation with one of the engineers. Apparently they were in a surly mood from people "commenting" about the sound, so I struggled to think of another topic.
I blurted the first thing that came to mind; "so, uh ... Who's your favorite painter?" He looked at me kinda funny and named somebody (I don't remember who) and added; "why do you ask?" I winged it. "Because what you do seems like the same thing, only you use sound instead of paint." Holy cow. It was like watching rain clouds evaporate. The dude positively beamed.
All I can say is that when we hit the stage, the sound was superb. He waved to me from the board, I gave him a thumb's up and life was sweet. (He probably waved at the complainers, too, but at least with me he used his whole hand instead of just one finger.)
Ever since, I've asked the same question to every engineer I've worked with, and it has a dramatic effect on their attitude (it works even better with other musicians). It's one of those things that has no downside, either, because it's honest, and the answer isn't the important part, it's just that I asked the question. Four little words. Does anybody mind being considered an artist? There ya go.
Whenever I read about people who regard engineers and soundmen as some kind of nemesis, I always think; "don't they realize that if there's anybody you don't want to piss off, it's sound engineers?"
To paraphrase
Benjamin Disraeli-Gear's advice about dealing with royalty;
"
Everyone likes flattery; and when you come to [soundmen], you should lay it on with a trowel."[/size]