I've gotten my Pono player to upgrade the firmware and I've added some albums. Neither of these tasks were very easy, but they weren't impossible, for a reasonably savvy end user to accomplish. Just the normal hickups of an early adopter process.
The Pono developers chose the JRiver Media Center to manage both the Pono player and associated audio files, and although it seems to work reasonably well, most problems seem to stem from the JRiver software. It's totally unreasonable to expect Pono to build a custom media center from the ground up to work with the player, so licensing a copy of JRiver (retail cost, $49.98--not cheap) is a good compromise. I notice that it takes a few steps, performed in the correct order, to get the JRiver software to recognize the Pono player. First, you plug the player in to the computer; then, you have to click through a couple of choices on the player (correctly) before the device is recognized by the OS and mounted by the file system (which I prefer--I like to actually see what's there). Upgrading the Pono firmware takes several clicks on both the device and on JRiver to work correctly, and unintuitively, you have to eject and disconnect the Pono player (assuming you have made the correct clicks) for the firmware to install. Some users had difficulty with this, but I was able to do it.
Basically, I think that most of us have been conditioned by iTunes to behave in certain ways and expect our media devices to do certain things, and unlearning this will take a few minutes. In many ways, JRiver and Pono are throwbacks to the early 00s, before iTunes obliterated the portable music media ecosystem. I don't have a problem with it, in my Old Skool way. In many respects, the Pono player is very much like an early 00s MP3 player (albeit, with more sophisticated DA converters), and those of us who hate iTunes (even while embracing its ubiquity) will like it.
I fully expect that all these glitches to be ironed out by the Pono team in the coming months, and I don't mind being a beta tester for Neil. (It's the least I can do to thank him for giving "Pocohantas" to the world.)
Will the Pono player sound "better" than my six (or seven) iPod Classics running 256 K MP4 files? I think so, but it will all come down to how the digital files are mastered. If you've used HDTracks, then you know that some tracks sound better than CD quality (44.1kHz/16bit), and others don't--it depends on what the record label provides. You can take a digital recording originally mastered at 16bit and blow it up to 192kHz/24bit, and sell it for twice the cost of a CD--but it will still "sound" no better than 256 K iTunes CD rip. This is the snake oil that critics accuse HDTracks of trafficking in (rightly so, though HDTracks is simply using what the record label provides). Will Neil Young be able to strong-arm the record labels into providing decent masters? Let's hope so. At the very least, one thing that I *have* noticed in the Pono store is that all tracks are at least CD-quality, including one album (Talking Heads, "Bonus Rarities & Outakes") that is only available elsewhere in the iTunes store in lossy format. So if you're like me and refuse to pay good money for lossy iTunes downloads, you can support Pono and your fav recording artists by purchasing lossless versions at Pono Music (and other hi-fi audio retailers like CDBaby and AcousticSounds).
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