My parents inherited a nice stereo from my great uncle when I was 13 years old but no one else in my family were interested in using it. It was a pair of Tannoy Dual Concentic speakers with 12 inch drivers, Revox A77 reel to reel tapedeck, Garrad 401 turmtable with sme3012 tonearm and shure v15 cartridge. I cant remember the amp. It got me really passionate about music.
When I was 21 I bought my own stereo from an accident compensation payout. Perreaux pre powers JBL speakers, Mitchell Focus 1 turntable and a Technics CD player (CDs were relatively new then). Unfortunately I always noticed the flaws probably more than I enjoyed the music. Every flaw grated on me. Recreational drugs helped me to focus on the music and the journey offered.
I upgraded often and at least every 6 months bought some new bit to replace a weakness in the system.
I have had Perreaux, naim, linn, plinius, creek, grail amps amongst many others
Speakers have included Yamaha ns1000s, B&W DM14s, Naim SBLs, Quad 2905s, Monitor audio gr60s, GS60s and now pl300s
Sources have been many varied including Linn, Naim, Kenwood, Technics, Wadia, Cambridge, Mitchell.
Current system is relatively budget comparatively with Computer to musiland monitor 02us to Audio-gd reference 1 to Linn Kairn(sps) preamp to bi-amped Linn Lk280/sparks to monitor audio pl300 speakers. I really like the sound and don't notice deficiencies as much now.
Headphone wise I use Shure se420 iems on the end of my iaudio X5, Ipod 160gb and Ipod touch 64gb. I discovered head-fi when searching for reviews of head phones for the iaudio.
I am about to embark on high end head phones as my stereo has been evicted from the lounge where it has dominated life for too long (from my wifes perspective). The system is moving into a back room which is small and compromised thus high end head phones are my only option for similar quality sound to what I have now. I have already decided on Sennheiser HD800 and an Audio-gd Phoenix amp.
Stereos and music have been a great but very expensive hobby. The 1 thing I have learned is that it is better to wait and not compromise on purchases rather than compromise because you feel impatient. There were many steps along the way that I should have missed gear wise. Head-fi is a great resource and my purchase of the audio-gd reference 1 was purely on opinion here. It was scary to purchase something I had never heard but wow was it worth it.