I have these IEM's and I found that the comply tips create a good seal.

I had trouble myself through media monkey. You can use the WASAPI output which still sounds good. Also you may wanna check out a different music player such as JRiver or Foobar2000. I've been using JRiver and I like it so far. Sounds a little better to my ears (but that could just be me). 

New to all this as well but ive been reading a lot on DAC's cause i want one myself.   Check this one out, pretty good reviews on it.   http://www.amazon.com/Audioengine-D1-Premium-24-Bit-DAC/dp/B006IPH5H2

Thanks for putting this up!

Yea I know...I just thought I'd throw in my two cents.

Comparing $400 dollar headphones (Beats Pro) to $120 headphones (ATH-M50's), these prices are from amazon. And there being not much of a difference between the two. It's a no brainer for me to go with the M50's. You'd have to be a complete tool bag to get the Beats!

Ok so I'm new to this website but I've been reading the forums quit a bit for some product knowledge. I've just recently got into the headphone realm and purchased a pair of ATH-M50's (I know these aren't the holy grail of headphones...but I like them). I've been looking at DACs to get for them...