Best place to learn about headphones is head-fi.com
I think the main thing to figure out is what headphones do not give you fatigue. Then how much to spend to on those non-fatiguing headphones. I hated my prior Senn 600 headphones because of fatigue with my Benchmark DAC3 HGC preamp/DAC.
I now have 2 headphone amps, a $3000 one and a $500 one. For headphone ONLY use the Topping A90 at $500 is highly recommended by me and is very close to the $3K Benchmark HPA4.. It is a neutral sounding amp. It goes great with my $3K Meze Empy, a warmish sounding headphone. I have not heard the $300 Meze 99 Classic but from what I have read on Head-Fi it supposed to be similar in sound to the Empy.
Your choice of amp will also figure in on the fatigue factor. I had a $2K headphone amp that gave me fatigue and it was replaced by the amazing Topping A90 for 1/4 the cost.
I think the main thing to figure out is what headphones do not give you fatigue. Then how much to spend to on those non-fatiguing headphones. I hated my prior Senn 600 headphones because of fatigue with my Benchmark DAC3 HGC preamp/DAC.
I now have 2 headphone amps, a $3000 one and a $500 one. For headphone ONLY use the Topping A90 at $500 is highly recommended by me and is very close to the $3K Benchmark HPA4.. It is a neutral sounding amp. It goes great with my $3K Meze Empy, a warmish sounding headphone. I have not heard the $300 Meze 99 Classic but from what I have read on Head-Fi it supposed to be similar in sound to the Empy.
Your choice of amp will also figure in on the fatigue factor. I had a $2K headphone amp that gave me fatigue and it was replaced by the amazing Topping A90 for 1/4 the cost.