Thanks for all the great responses so far! I'm interested in good SQ, but only to a certain point, and I think I've hit that point as HamilcarBarca and Lorspeaker have pointed out. Unless there's a headphone, dynamic or electrostatic, with a massive increase in SQ within my budget (<300 dollars, preferably less by buying secondhand), I'll just settle with what I have now and learn to appreciate them. Maybe one day when my ears are extremely sensitive, I will invest in a >1000 dollar rig, but for now, I'm fine.
However, I am interested in a <100 dollar portable amp if it will significantly improve the SQ of my M50s and my 225i. I listen out of my iPod nano and my Dell Inspiron laptop. Should I even bother looking at amps at this price range? If so, does anyone have any suggestions?