I've come to the conclusion that I need to buy headphones, but every set I've worn in the past has become unbearably uncomfortable before long (over-ear headphones make my outer-ear cartilage feel bruised and ear buds make my ears ache

how do you guys deal with that?

In ear monitors do hurt after some time. My preferred head phones are soft-touch material ear-muff based headphones. I use Skull Candy's Uprock model (http://amazon.com/Skullcandy-Uprock...) . Good price, greate quality, not too bulky and are comfortable to use for hours on end

I have had that issue, I use just apple ear pods now. Doesn't work as great if your trying to get stuff done, for some reason people think it's ok to bug you

For home or use the storm sirus, haven't had any ear pain yet.

For on the go I bought the sennheiser momentum 2.
Ducking expensive, but the clearest sound ever and the over the ear cups are big and soft. No ear pain thus far

Only the headband can irritate a bit after an hour or 2

Had problems with lots of ear buds. Bought skull candy ones randomly and they didn't make my ears hurt even with 6+ hours of wear. Decent sound, inexpensive. Change the rubber part to fit your ear.