whatever annoys me the least over time. Then build a rig around that. I wish I could go back in time and just tell myself to save up money, buy that, and build around it.

This is my personal flowchart since I've opened my eyes to head-fi. It all began with mid-fi purgatory.

K701 : I bought this headphone because of this. Shame on me.
http://41.media.tumblr.com/tumblr_lk2c2en6xd1qics1qo1_500.jpg
I had it paired to a Little Dot MKIII, which was my first headphone amp. Back then I had no reference to compare whether this was a good or a bad match, so it stayed in my collection for several months until I decided to try out other stuff.

DT880 (600 ohm) : Much better match than K701 on the LD MKIII, being a high-impedance headphone. This is when I learned the general rule of thumb that OTL tube amps have high output impedance, and that you should pair them with high impedance headphones. Which lead me to...

HD650 : Even better than the DT880. I was quite impressed. That's when I asked myself, can things get even better from here? Soon I found myself craving for Senn's flagship HD800, wondering how good it could possibly sound.

HD800 : What? While I was impressed by its superior transparency and soundstage over the HD650 at first, I realized I couldn't stand listening to this headphone for more than an hour due to listening fatigue. Didn't take me long to start missing the HD650 I had. That's around when the ortho craze started with the advent of Audeze and Hifiman. People were raving about how the new planar magnetics LCD-2 and HE-500/6 beat the crap out of all the traditional dynamic headphones out there. Which lead me to...

LCD-2 Rev.2 : I knew that my LD MKIII didn't have what it takes to drive these, so I also bought a Schiit Lyr upon its purchase. A lot of folks were recommending Lyr for orthos, and it had a reasonable price tag so why not. Although it was a lot heavier and uncomfortable than I had imagined, I was pleasantly surprised by its sound. But not long after LCD-2 was updated to Rev.2, then came...

LCD-3 : Okay, I didn't stick with LCD-2 Rev.2 for long because the release of LCD-3 that soon followed tempted me to buy it out of FOMO. To be honest, at double the price tag, I didn't hear a lot of difference and it left me wondering if the improvement was worth it. Then I thought maybe my Lyr wasn't up to the task, so the Lyr left and was replaced by Burson Soloist.

Fostex TH900 : I was tempted to buy this one largely because of its sheer beauty. In retrospect, I don't think this was a bad purchase. The sound was somewhat congested compared to the open-back LCD-3 but it was overall cleaner with a fun V-shaped sound sig. But I didn't think it was an ideal match with Burson Soloist, too bright on that setup. That's when Romy (Muppetface) recommended the Eddie Current ZDSE for the TH900. I said "but the TH900 is only 25 ohms and ZDSE is an OTL amp!" Then I learned that the ZDSE, despite being OTL, only has an output impedance of 3 ohms at lo-Z setting. Goodbye Soloist, hello ZDSE. It was the first headphone amp purchase I consider truly high-end.

Audio Technica ATH-W3000ANV : The W3000ANV didn't replace the TH900. It was more closed-sounding than TH900 but more euphonic and the same time, and the matching with ZDSE was beautiful. However, at the end of the day I found myself preferring the TH900 which is a technically superior headphone. And speaking of technicalities, BournePerfect told me that HD800 is actually the best headphone to pair with the ZDSE. I said "but it was cold, harsh, lifeless, brittle, analytic, and fatiguing!" He told me that the ZDSE tames all that with its euphonic sound sig and takes the HD800 to another level. So...

Sennh eiser HD800 : There I was, back with these headphones I had abandoned years ago. And he was right, in part. I saw a new side of HD800 that I couldn't see before, and the ZDSE made me appreciate how high the HD800 could scale. I thought the ZDSE/HD800 was end-game for me. However, not even the ZDSE completely took off the HD800's sharp treble. It was still present, and made me cringe at times. I knew I couldn't stop here....

More to come.