The Best Audiophile Earphones headphones and Amp

I just recently plunged into the world of headphones and am having a slight problem adjusting to the new listening experience. Generally I find headphones to sound, well, like headphones. The soundstage is small and doesn't sound as big and airy like loudspeakers. I also find headphones to be uncomfortable when used for long periods.

If I can get over all the caveats with more training(hopefully), I might want to explore Stax in near future. Is the Stax SR-007Mk2 or SR-009 a huge improvement over the Beyerdynamic T1 in areas of musicality and transparency with significantly higher comfort levels and lower listening fatigue?

There is no definitive "best" of anything. There are way too many variables involved. The "best" you can hope for is to find something that works well in your system. You can then say it's the "best" for you until you find something you think is better !!!!

I've been looking for a new pair of phones for use with a Logitech Squeezebox Radio.

I have Stax headphones on one of my system and am looking for something that will sound similar in terms of natural non-fatiguing sound especially at higher frequencies at least off the SB radio.

I have heard various Sennheiser, B&W, AKG, Grado, and one or two Audio Technica so far.

So far I like the AT best followed by Sennheiser.

Newer Focal phones have caught my attention. I have heard Focal speakers sound quite ES like and phones are rumored to have similar sound.

Would Hifiman phones be a decent match for a SB radio?

I've also heard Audeze and thought those had potential but pricey and maybe overkill for a SB radio.

Open for suggestions, ideas, opinions on which way to go with Stax as my reference sound.

As an owner of a high end system, you are undoubtably aware that there is no one single "best" in any component category. There are plenty of headphone users that like electrostatics and many that don't, and there is disagreement about the merits of any contender.

I own an Stax Omega II, Mk. I, and a Blue Hawaii Special Edition amp. I like the sound, but it is far from perfect. The Blue Hawaii amp is, to me an improvement over the tube amp that came with the Stax phones, in most respects, but, it does exaggerate surface noise on LPs a bit more than does the Stax amp (also adds a tonal "ping" to ticks and pops), which I don't like. I heard the Stax 009 model headphone with a Woo amp, and did not prefer that sound. A friend heard the 009 with a Blue Hawaii amp in a shootout with the Omega II and preferred the Omega II (not as bright). But, most listeners prefer the 009, so again, it is a matter of taste.

For a much less bright sound and a richer overall tonal balance, I have heard Audeze headphones that I liked. I can easily understand how someone could prefer this sound to the Stax sound (and save a LOT of money).

My experience so far with tube headphone amps and Sennheiser HD600s leads me to opine it all comes down to tubes, fuses, isolation, cryogenics, cable cooking, and a lot of other things. Not to mention removing the HD600 grills and foam pads inside is a step in the right direction.