Buying a pair and making them comfortable with foam tips is a no-go, I tried Comply and they need to be replaced way too fast (I blame my gross ear canals, they output metric tons of wax.)
Keep a box of q-tips in your bathroom, use them after your shower. Problem solved, and your ears will be more comfortable.
I'd definitely check out the V Sonic GR06
Never heard them, but I'm on here and Head-Fi a lot and these are a very popular reply to the question... just backing up Dynamite.
Is there a rough price ratio for amps to headphones? Like, if you buy 500 dollar headphones, you should be looking at 100 dollar amps, then 50 for $250 headphones? Or is that too difficult to do since portable amps are different than desktop amps?
I really think it all depends on what you get. There are expensive amps that aren't worth it, and there are cheap amps worth much more.
Just by judging my favorite amp/headphone combinations... for cans it's gotta be close to 50%.
Spend $1200 on some GS1000s, spend $600 on a WA6...
Spend $600 on some RS1s, spend $300 on the O2/ODAC...
For IEMs, at least anything under $250, I wouldn't say they need anything more than an E6 (gasp!)
Mostly alternative, some electronic, lots of talk podcasts :/
I really like MonoPrice's offerings for those types of audio, honestly. The only other under $100 pair of IEMs I've found that are worth the money is the Altec Lansing UHP326's, but they're discontinued and wouldn't work well with electronic music.