[riot507]

If you're going for IEMs, i recommend the head-direct re1s. I wasn't really a fan but, the dt770s suggested earlier is popular here if you're into bass. You can then spend the rest of your money on a decent portable amp. The mini^3 is an awesome little amp for it's price. PM misterx for more info. If you're into rebates, I would personally grab the d2000s shipped for about ~185 bucks on ebay if you do the 30% off microsoft live thing and spend the remaining ~120 bucks on the mini^3.

 

[Meta-Fi]

From what I've been reading by searching around the IEM forum, the 2 main standout's at around 300$ are the westone um2 and the shure se530
(although admittedly I have no idea on the legitimacy of buy.com)
If anyone personally owns either of these I would be glad to hear your opinions..although maybe this is straying too far off topic/wrong forum
Pm's are fine by me if that is the case
Anyway thanks to all for the assistance, I feel at the very least I will be making an informed decision.