I suppose I should add musical tastes: A very wide range of music sans hip-hop/rap. Some classical on occasion, but not that much.
To give you an idea, my most current rotation includes: KMFDM, the Pogues, Garbage, VAST, Conjure One, BT, Colin Hay, Poe, Rush and NIN...
The Dr150s seem really intriguing. I had never heard of them, but after reading several threads, they seem to be outstanding, or at least the FOTM. Might be the compromise I am looking for, but at $150 + shipping, a bit more than I wanted to pay, but I suppose that's head-fi for you. I have to say that I love that you can easily upgrade the stock IC.
However, I've been re-listening to my MS1s on and off all day. I've tried the MS1s with both the stock comfies and the bowls. I am beginning to think that maybe the discomfort I'm feeling from them is actually in large part, listening fatigue. I don't know if it's their brightness or their aggressiveness or a lack of soundstage. I just seem to get a headache after listening to them for a couple of hours (at low volume).
Maybe the real problem is that the Grado sound isn't for me (at least not for extended periods of time). If that were the case, it seems that the DR150 might be similarly aggressive and exhausting. Maybe the AD700s (which I can get for a few buck more than $100) might be better choice given their comfort ratings and their expanded sound stage (or at least from what I've read in the forums). I was also looking on the forums about the HD555 which have mixed reviews. I've owned some cheap Sennheiser's in the past but with that caveat, I was always underwhelmed by them. They were somewhat murky in the bass, or just flat overall... or maybe, what I'm trying to express, is that I found them boring.
The AD700s seem like they might be what I'm looking for. That being said, has anyone done a comparison between the DR150s and the AD700s?
Or maybe a better question is that if I didn't like the MS1 style of sound am I going to dislike the DR150 sound?
Oh and on a completely random aside, I just wanted to thank all of your for your help and suggestions, I really do appreciate it and your time.