Great post Atticus!
I think it highlights one of the real issues with Hi-Fi - the focus on equipment over the music. Over the years it's easy to get wrapped up in the technicalities and lose sight of what got you into the hobby in the first place.
Much like you I started out with a simple system and made many upgrades, going through every brand under the sun and eventually I realised I was more concerned with the gear than how well it reproduced music, how much I actually enjoyed it.
Nowadays I've become very used to hearing through the equipment, I know within seconds if I'm going to like a system or not - hours of listening isn't necessary in my view - it just gives you time to adjust to things that may not be right (to you) and accept them rather than finding something more suited to you in the first place.
When designing speakers I know from the first couple of bars what I need to know, will then grab a couple of familiar pieces of music which highlight those particular strengths or weaknesses, play them to confirm and I'm done. The engineer hates it but I've found I rarely make a bad judgement in doing so. If I have to listen to more tracks to find a fault then we're usually at the point I'd consider the speaker to be about right - if I'm just listening because I'm enjoying it we're onto a winner!
We have plenty of people in the office who aren't into Hi-Fi, and also a few accomplished musicians (though our Warehouse drummer's version of "music" is a stretch - have a listen to him play on "I Defy's" version of "Dead For Good" on Youtube to hear what I mean!) - I get them all to listen to new product and most of them pick up on any problem areas straight away, and then say "but what do I know?". This really annoys me - you know as much as anyone else, what you hear is as correct as any "expert's" opinion!
For what it's worth I think I know the problem you're highlighting with your system, it's lacking musicality, when everything is right you'll stop having to listen for fine detail, it'll just be there at the right level to listen to or ignore as you see fit. I think electrostatics may well be a good option - I heard the Quad ESL's at vegas a couple of years back and still think they beat most other systems on display there, they were just natural sounding and easy to listen to (which can sometimes be taken as a criticism in Hi-Fi for some reason!) I wouldn't worry too much about the bass, while it wouldn't have the impact of a big cone driver it does play a tune very well.
My old Hi-fi all resides in the office nowadays, I take home bits and pieces to try out with new product and the systems I find work best for me in my house are rarely the ones that get 5 Stars in reviews - The Compact 1 + Naim UnitiQute that we used at the Bristol Show worked perfectly in my smallish listening room (people seemed to love it at the show too!) so that's what I listen to at home now. I've got access to anything up to our old AE5's which are awesome speakers but just wouldn't work, 10 years ago I'd have given my right arm to get something like that at home - how times change!
I hope you finally find what you're looking for one day, trust your own ears!
Jim.