First of all, let me express that I'm not asking for which headphones are best in general and that I'm asking this question because Mac users tend to have taste that matches my own. Thus, I feel that the Apple S/E is an appropriate place to discuss headphones.
I have read many, many, reviews of headphones over the past few days and I've listened to several of the different models that are available at Bestbuy and the Apple Store (those are the only places near by that will allow me to actually listen to different models across brands).
However, I remain unsure as to the most suitable headphones for my specific needs and have thus come here with a (I believe) specific set of criteria that the community will be able to help me fill:
I'm willing to spend up to $300 but preferably no more. I really enjoy listening to a range of music so I consider this a pretty reasonable investment. I don't take the time to use .flac or other ultra-high quality formats because I dislike having to complicate the music experience. I realize this will hamper the performance of my headphones, but it's a hit I'm willing to take.
I don't travel frequently, once or twice a year by plane, but I do spend a lot of time in cafés and coffee shops while I work. This makes noise cancellation a beneficial feature but it is not absolutely necessary, especially with over-ear style headphones.
I tend to listen to music while I go to sleep but I almost always sleep on my back so I don't think headphones will be a major problem with comfort here though please correct me if I'm wrong.
Because I do leave home quite often for work I would like the headphones to fold neatly for storage in a messenger bag. The one I use isn't very large, but it fits a MacBook Air in a Tom Bihn sleeve along with a power cord and an iPad with room for several notebooks and some extra space, so I believe folding headphones such as the Bose Quiet Comfort 15s and similarly sized models will work nicely.
When it comes to sound reproduction I'm not looking for excessive bass and I rarely move the volume over about 50% (I have pretty good hearing so it's usually not necessary to) and that means that headphones that suffer from sound degradation at higher volumes aren't automatically out of the question as long as that degradation isn't a sign of poor quality.
Finally, I absolutely hate for a product to get a "worn out" look quickly. I expect these headphones to last at least 5 or more years and with fairly constant use they will naturally show signs of ware after a few months. My issue is, for example, a pair of Beats earbuds that I bought 2 years ago completely fell apart. The joints wore out and the cord was frayed in several places. (They were purchased at an Apple Store, so I'm pretty sure they weren't fakes). I expect companies like Sennheiser have a much higher level of quality than Monster (hence the higher price), but higher price does not always mean better, so that's one of my primary concerns.
If this question won't fit the Q/A style please let me know and I'll just remove it but I feel that I'm asking for pretty quantifiable information regarding a product category. So, if any more information is necessary please let me know.