So updated impression after 1 month with the IE80 (roughly 100+ hours burn in now). Disclaimer: my source is a rooted Samsung Galaxy Nexus, I listen to mostly mp3s and would live in perfect harmony with 320kbps VBR, and I am fully aware of how unworthy I am by headfi standards.
Initial fit issues aside, I'm about 95% satisfied with the stock large flange now and my ears no longer hurt from trying to push the housing to form a seal like at the start. I would like to give stuff like Complys a try but I'm not really keen on shelling out even more money on a regular basis. The cable has also become much more flexible compared to their out of the box stiffness such that I have no trouble wearing it over the ear without the ear guides (the ear guides made the fit even more terrible for me at the start so I don't use them). Even though I had some reservations about the size of the housing and having to wear it over the ear, I've now become accustomed to doing so and the IE80 feels pretty close to the X10 in comfort.
When I first tried these the bass sounded really boomy and hollow to me with the bass dial turned up, in fact half way through I almost decided I wanted to dial it down to a minimum which is surprising given I come from Monster Turbines and Klipsch X10. Turns out it was because I had some 3D effect settings on from when I had my X10 - which had a huge mid bass hump and didn't really sound any different with the 3D effect turned on. Before my purchase I had simply assumed that the bass dial meant MOAR BASS, or mid bass as I knew it, but what it actually seems to do is shift the bass curve left towards more sub bass - so much so after a week with the dials on max it became near headache inducing. I'm now running with the dial solidly in the center and I think that's where it'll stay, with no EQing.
Speaking of EQing, from memory it seems like the IE80 is far more responsive to EQing than the Klipsch X10. It's also got a much more forward mid and better highs - if I dial down the upper registers on the EQ it reminds me of what the X10 sounded like (not a surprise given the X10 FR has huge rolloff at the high end). Listening to some songs that I've probably heard 1000 times (I don't expand my library very often) I began noticing things like cymbals in the background while it's going through some bass heavy sections; basically things I don't really think i've noticed before with the X10. Some of the poorly encoded MP3s in my collection also started revealing themselves with the IE80, where as the X10 was much more forgiving. The IE80 is also more sensitive (16ohms vs 50 for the X10 I believe?), so it's more prone to hissing and noise from bad encodes.
In terms of sound stage etc I now think that the IE80 does a far better job than the X10, though my memory could be playing tricks on me. Either way I am not a purist and would happily apply what software crossfeed I could get my hands on to move the sound out of my head even if I was using regular headphones. If you want the whole 'sounds like speakers' experience I don't think there's any possible way to do that without crossfeed no matter what you've got.
I found no use for the included cable clips so far because there is little to no noticeable microphonics to me. I am also not using the carrying case because it's a chore to wrap it around properly, plus I found that the large tips actually get squished if you don't take them off before storing the earpiece. With the cable now spending a bit of time in my pocket it is starting to twist and tangle a little bit, though nothing like some of the cheaper headphones I've owned in the past.
One obvious weakness of the IE80 is the poor isolation. Normally with the music up it's not really an issue (people have to wave their hand or tap my shoulder at work), but when playing quiet passages that guy sitting next to you yapping on his cellphone becomes part of the concert. Granted this is a pretty well noted problem and it wouldn't sound like the IE80 if it wasn't for the semi open design, but given the amount of time I spend on transit it's really too bad I can't have the best of both worlds. On the plus side it's a bit safer to walk around with, though that's largely negated by the amount of dog poo on the crosswalk and my habit of just looking at the smart phone screen while walking. At times I also wish that the IE80 comes with remotes so I can at least skip tracks, though the option to purchase IE8i cable is always there (for about 50 bucks from Sennheiser UK's website).
Overall for me I believe that this was the right choice at my budget of $300. At full MSRP however I would've taken a more serious look at the competition and could have easily gone with a different set given my noisy listening environment. (sorry I should sound more excited, but it's 4 AM and I should be in bed)