Pre Head-Fi: I had a Defintive Technology Home theater sytem with Tower speakers. Source was and remains an Arcam DV88+
Than we had a baby ...............and then we had another baby ........
Post Head-Fi I now have, no tower speakers and:
Phillips HP1500 Dolby headphone processor with HP1000 wired headphones.
Sennheiser HD650 with Headfive Amp.
Stax 3030 system (E-Bay, second hand)
Sennheiser CX300's for my Sony NWA-1200
Thanks to the advice here, I haven't had to upgrade anything and I'm using everything I've bought. Total spend is €1,200 or about $1,600.
Next up I'm waiting for the Yamaha ysv-1 processor which is supposed to blow Dolby Headphone out of the water.
In my weaker moments I think about upgrading the Stax to an Omega II set up or maybe a HE60/Stax setup, but I find it hard to justify spending about 5 times as much as I did the Stax 3030.
Funny thing is, I don't really miss those tower speakers all that much!