Well....
Lossless - Because I am real picky when it comes to music. My other life (read: don't make any money at it) is as a recording engineer/musician. Just the idea of compressing audio files when HD space is so cheap makes me nuts. And yes, I can hear the difference.
I forgot the contortions needed to make m4a or mp4 files play in Premise/Windows Media Player. You have to get WMP to play it, then premise will. It's a long drawn out process.
As for Internet Radio, I haven't tried anything for quite some time because there seemed to be a period of time when nothing would play, so I gave up. I'll have to try again soon. But there are lots of things out there like Pandora, Shoutcast, etc.
Limited automation: Time, lack of money, lack of scripting knowledge.
I got the iPhone almost 2 years ago because I needed a smartphone since I am a one man business and I needed to be able to not only get email, but deal with customer contact info and calendars for the business while is was out at client sites. And my Motorola Razr just wasn't cutting it
There was a great deal out there at the time for refurbished iPhones. Sealed the deal for me. Now I wish I had gone for an Android phone
Honestly, now all my rippped music is playing in Premise. The lack of tag info is really not a huge issue. I just KNOW it's supposed to be there. But the original issue that started this thread is solved. Don't use UNC paths and everything works.
But I am finding that alot of my media consumption is moving to online sources and I'd like t o integrate that into Premise. The idea of buying a piece of hardware to play internet radio when my Premise server should be able to play them seems wrong