Thanks for all of the responses. I guess I should clarify what I was saying above: it isn't that there aren't differences in each system or component I swap out, it is I can't really make a quantifiable "upgrade" based on amplification at this point. Sure, I heard more neutrality and a bit more detail with the Herron upgrade. But did it sound really better? I could be happy with either. Same as the Sixpacs vs. DNA-125: each sounded great in their own right, but spending twice the money (used) on the Sixpacs didn't significantly "upgrade" the sound, it just changed the flavor a bit. I guess this is part of the trouble with building a system for a newbie: I don't know what sounds good until I have heard it. What I am trying to accomplish: a cleaner, more resolved sound, with a nice soundstage and "I am there" feel.
With that said, I went listening at area store to some setups, just to get a feel for how other systems sounded to mine. First setup I listened to: a Classe CP-700 pre, Paradigm Studio 100 v.3 speakers, powered by a Rotel! amp (I have no idea why). It sounded horrible-a grainy, SS sound. They hooked it up to a Bryston 7B-SST, and it was better (more control over the woofer) but my system sounds much more liquid, more detailed, and lifelike (their system was bright and not as musical-I didn't like it). I then listened to a nice set of $10K ML's (with the powered sub) powered by a Jolida integrated and mid-fi Denon digital source: this system was more detailed, but still tinny and less than pleasing. Not much of a soundstage (the Jolida seemed like a suspect choice for powering $10K speakers). When I got home and listened to my system, I thought "wow, this sounds pretty darn good!".
Not having other systems to listen to, it is hard to determine what a really nice sounding system feels like. With that said, the original intent of my question was to determine whether it makes more sense to pair $5K speakers with $2.5K amplification than the other way around. Thanks for all of the help.