[Rex24-7]

I've been looking through headphones and IEMs for 2 weeks straight. This is ultra frustrating, similar to buying a car but not being able to test drive any first @_@. I figured I really needed to ask the experts what I should do. I have owned the Sennheiser HD25-1 IIs for over a year now. They still sell for around $250.
 
Pic for reference:

 
 
What I like about them:
1. They are neutral sounding. I like to think I am hearing the sound as the producer intended it.
2. They have deep punchy bass. My main genres are trance and metal, and this phone supplies the right amount of bass for them.
3. They are all rounders. When it comes to music, I can be quite random. Power metal one hour, Slow jazz the next hour.
 
What I dislike about them:
1. They are uncomfortable with the glasses I wear. I don't really need to describe pain, do I? 
2. They do not have enough sound stage. While I find myself gravitating towards signatures of monitor-type equipment, I recently desire a more open experience.
 
In the beginning, all I wanted was an IEM equivalent to the HD25....with more sound stage. But still good isolation. Kind of a unicorn. So then I thought....should I buy one pair of nice IEMs ~$400, or I should just buy cheaper IEMs with isolation and then larger over-the-ear headphones with sound stage to get the best of both worlds? Which scenario and phones would you recommend?
 
Top choices for me so far:
Portable use only:
Vsonic GR07: Seems to have the right signature, though maybe also recommend something with more isolation.
 
Home use only:
Sennheiser HD600: I constantly hear how much sound stage they have and how they are more comfortable.
 
End all, be all IEM: Honestly, there are too many to list.

 

[KG Jag]

The NAD VISO HP50 for on the go.  See:
 
http://www.innerfidelity.com/content/i-love-these-headphonesthe-nad-viso-hp50
 
and
 
the HD 600 or 650 for home with a decent amp (the affordable O2 will work fine).  See:
 
http://www.head-fi.org/t/634201/battle-of-the-flagships-58-headphones-compared-update-audeze-lcd-2-revision-2-6-4-13#user_HD600 
 
&
 
http://www.head-fi.org/t/634201/battle-of-the-flagships-58-headphones-compared-update-audeze-lcd-2-revision-2-6-4-13#user_HD650
 
Beyond that--headphone comfort is a very individual thing.  Everyone has a different head size and shape, as well as different sensitivities and levels of sensitivity.  We can point you to headphones that are generally considered to be comfortable and mention others that have garnered complaints for being uncomfortable.  However, the only way to know for sure is to wear them yourself for a time equivalent to your longest listening session.

 

[Dragonzeanse]

I've used the Sennheiser HD 600s with glasses on and they're great. A good pair of IEMs that would compliment the HD 600s if you don't want the same sound signature in a more portable form factor would be the RHA MA750. They might sound veiled in comparison to other headphones, but they have just enough treble to prevent them from sounding dull. If you don't like them at first, try them out for a little while, then if you still don't like them, return them. They're comfortable with glasses, too (but can only be worn over-ear).

 

[Za Warudo]

I would not recommend the HP50 for glasses wearers. I had it for a few days and couldn't wear if for more than 1 hour without taking a rest. The pads compress too much and so the cups end up squishing your ears against your glasses.

The HD600/650 are no problem unless you have a wide face.