The HE-300 is not a very neutral nor good sounding headphone. It sounds distorted, slightly tinny, and the over all sound signature would not last more than 1 track on my setup. The AKG K550 is awesome sounding, but has one comfort issue. The headband is very sharp so if you do decide on the K550 you may want to invest in some more padding for the top center of the headband.
Take a look at the charts below:
K550
http://www.innerfidelity.com/images/AKGK550.pdf
HE-300
http://www.innerfidelity.com/images/HiFiMANHE300.pdf
See how the HE-300 is not very flat especially toward the treble in the frequency response. This gives it a very uneven sound. Comparing the 300 Hz square wave responses also reveals that the HE-300 does not reproduce the harmonic frequencies of 300 Hz very well indicating poor vocals and instrumentation. The K550 300 Hz square wave response is almost ideal for a dynamic headphone. Now look at the Total Harmonic Distortion ( THD % ). See how the HE-300 is all over the place and above 1% well passed 1 kHz? That is exactly what I heard when I ran them through the paces.
If you want to go to an HE headphone go up to the HE-500. Those are an amazing headphone and will probably be my next purchase otherwise the K550 will do just fine. I could listen to just about any track with them and be pleased.