I have been using these for the past couple of years and they are pretty amazing. My ears do get a bit sore after using them for an extended period of time (3+ hours) but that hasn't bothered me too much. I have been using new ear pads for about a year now (I ordered some last August) and they're still in pretty good condition). The thing about new ear pads is that they make the headphones feel brand new again. My pair was purchased by my dad almost twenty years ago and they're still in great condition. I have heard from my cousin who has purchased a few pairs of these is that the ones they produce now are inferior compared to the pair I own because they're made of plastic and not metal anymore. I have another cousin who bought these and they are just about equal sound-wise. She also says her ears don't get sore from them, but that they can get really hot after an extended period of time.
Im not familiar with the exact model you mention, but I'm the biggest advocate of the HD280 Pro's that you'll ever meet. I got my pair like 7 years for that exact same price, so I wouldn't suggest holding your breath too hard for a sale but they're the best headphones you'll ever have.
I have the Sennheiser HD280 Pros, which are the closed back, slightly less expensive equivalent to the HD555's.
Personally, I prefer closed phones for gaming, movies, and studio monitoring. Open phones like the HD555's are better for listening to music, as they'll add some warmth.
Though, the HD555's are a lot more comfortable.
Definitely go with the Zalman clip-on. Or, be ghetto like me and use a separate mono headset draped around your neck.