My Pono experience has improved significantly, in every way, since my initial post (#9 in this thread.) Here's an update.
1) The sound is really good. I am not a big believer in "burn-in", especially for solid-state components, but I'm finding the Pono is more clearly a step up in sound quality from my iPhone now. I am happy to explain that in terms of me "getting used to it" and coming to hear the nuances, rather than the device itself somehow changing.
2) I can live with the software now. There are still quirks, and things that aren't so elegant, but with only slightly more hassle than iTunes, I can get music on and off it pretty reliably. The SD card appears on my desktop (Mac), and I configured a smart library to transfer over the files I want onto the unit's main memory.
3) I still don't see the Pono business model working in the long run. If the objective really is hi-res for the masses, they've got to compete on price with iTunes - same price, better quality, and then *maybe* the kids will start to tune in. Don't the artists want us to listen to them their music the way they intended it? So, why the price wall? Maybe Neil, for all his clout in the industry, just isn't Steve, and the labels are having their way with their customers, as usual. Alternatively, if the Pono store's only ambition is to stay stuck in the nice audiophile market, please provide us with information on provenance! What do I get when I pay twice as much as iTunes for Foo Fighters album? Is it the same mastering as the iTunes version, just at higher resolution? Or, is it actually mastered differently?