I'd go for a transformer on the output of the DAC. The output stages don't always deal well with 12-24ohm loads (even 120-300 may bog them down) and the transformer will reduce apparent random noise. To run IEMs directly you will need to run the output stage at a really low gain: you may find yourself with a maximum output that is so low that hum pickup becomes an issue again.
A bunch of people make 5K:8ohm transformers that should work well for this. I'm quite fond of my radio-shack 1k:8ohm transformers, they are worth at least $2.50 each*. Xicon sells similar (maybe they are the OEM for radio-shack? they look the same) units through mouser, at similarly sweet prices. For what the alternatives cost (like $20 each and up) Im not sure Id upgrade.
*I use my transformers on the volume-controlled line out of the Iriver IHP120. The idea should transfer to a home system with good gain structure nicely.
Edited by nikongod - 4/25/11 at 11:54am