Some people like high end headsets...there is nothing wrong with that. To each his/her own.
I'm really happy with the Cane Creek ($40) on my fixed. It is sealed, smooth, and with proper cleaning and maintenance (which is sooooo easy) I cannot see it last less than the life time of the bike. Does not feel as smooth as a non-sealed loose ball headset though.

I'm on 8 years with the Campagnolo Chorus headset on my road bike ($40)

For my cyclocross bike, I just keep replacing the $16 Ritchey headsets as needed (every 2 years or so) since it takes so much pounding and slings from mud and water, but I still clean it every few rides or so to get the dirt out. After a while, it can only take so much, it gives in, and it gets tossed.

I feel the key to long headset life if regular maintenance...higher end ones will be sealed and will go longer without regular service, but after rides in heavy downpours, or lots of mud, they need cleaning. The riding conditions also play a major role inthe life of a headset, of course.