Brian, as a rule I run direct to the P.A. unless I require big stage sound. Actually, even then I still run direct to the P.A., I just also monitor myself either through my amp or through an 'FRFR' - in my case the Alto TS110A.

Working with the 11R is helped immensely by having an editor but at the very least, as Rushian mentioned, the elevenhack program will allow you to quickly audition sounds... it's very useful.

If the distortion sounds like an icepick... and I'm going to assume other things don't sound that way through the same headphones (personally, I find guitars generally sound kind of irritating through most headphones), then you'll need to consider pre- and post-EQing to round out the tone. Do yourself a favor and get the Singtall Superpack... you can't go wrong with that. The only issue you may have with it is dealing with an embarrassment of riches... there are a lot of presets to try.