Can headphones ever be as good as high end stereo?

Headphones are way easier to try and audition than a home system.

The beautiful wall of sound will be different, more encompassing and less in front of you. Some pricey audiophile phones and/or phone amps may attempt to simulate a soundstage and imaging like a good speaker setup.

You might like it better or worse. Speaker soundstage and imaging are the aspects of sound that will most likely be impacted. All the rest could well be better for much less. It all depends on what you value.

I tend to still prefer my speaker setups when I can listen to them but headphone listening time is on an uptrend for me for practical reasons.

I listen a lot away from the house via Plex Media server, which is a very nice very low cost, high quality option for listening via computer audio and mobile devices.

PLEX mEdia server and web site enables listening via any web browser for free and there are mobile apps for Google Android and Apple mobile devices for only $5 per platform. Its a no brainer to try this alongside ones big buck home system these days and see how it goes.

Yet another reason why the future of audiophiledom as we know it looks to include a lot of change and/or expansion from the old, proven, and often quite expensive tried and true ways.

BEing able to listen at volume you want without disturbing others alone is a great reason to add headphone listening to ones arsenal, and hten just let things play out from there as need be.

The upside of your situation is the recent incease in options of high-end headphones and amps; Stax has more competition. I tried a few at axpona and was really impressed with Audeze LCD-3. The downside is the presentation of headphones is in one's head and does not change as you move your neck. I do not think quality is going to be the issue so much as presentation. That is up to you.

You can, indeed, get great sound from a set of headphones. The experience is quite different, and I personally don't think it is worthwhile trying to chase similar imaging with phones--I accept that phones will present sound as coming from inside my head rather than imaging like speakers (crossfeed circuits, binaural recordings, headphones with drivers that are placed to mimic speakers, etc. really aren't convincing).

I have Stax 007 (Omega II, Mk.1) phones and a Blue Hawaii Special Edition amplifier/energizer. I like this premium combination a lot. I have also heard the 009 phones with this setup. The 009s have better bass, better dynamics, and a more extended top end. But, this comes at the price of sounding brighter and somewhat thinner in the midrange than the 007. Hence, there are tradeoffs and I would not declare one better than the other sonically. Both are reasonably comfortable (the 009 is heavier). The Blue Hawaii amp driving Sennheiser HE60 phones (discontinued) also sounds quite good--smoother and more natural tonal balance, but slightly duller in dynamics than the Stax phones.

For a quite different sound--much warmer, but lacking in the clarity of the Stax phones--I like the Audeze LCD-XC. This closed-back version of the Audeze planar magnetic phones is very nice sounding to me. Audeze phones with a really good amp, such as the Viva headphone amp, would make a killer system. The Abyss planar magnetics sound good too, but, I did not think they warranted the really high price and they are somewhat uncomfortable to me.

For a much cheaper alternative, I liked the top-of-the-line Mad Dog headphones (closed back).

To me, Stax phones border on being too thin and bright and are quite demanding of upstream components. But, apparently, many other listeners demand even brighter sounding phones. If you are one of them, the Sennheiser HD800 headphones will deliver a brighter sound. I personally don't like these phones at all, but, like everything else in audio, this is a matter of taste. You should at least audition these phones and their sonic opposites (Audeze) to get a measure of the range of choices.

Good regional audio shows present great opportunities to hear a wide range of gear. Most shows have a big gathering area dedicated to headphones. This is usually one of the highlights of the show--everyone is friendly and helpful, everything is available for personal trial and the whole scene is enjoyable.

I have older Stax and newer Sennheiser, Audio Technica and Klipsch phones/buds. Each is different and has its charms. If you like the sound of Electrostat speakers or Maagnepan, you will like the Stax and/or other newer ES or planar magnetic headphone options out there as well. Sennheiser tends towards a warmer less bright non-fatiguing kind of sound overall. Klipsch and Audio Technica are both good as well but sound more like most other good phones.

In some ways....better