Long post, my thoughts on the Zune Software NOT hardware. There has been a lot written about the actual Zune Device, but not much about the market place. I just wanted to get other people's opinion, if they have tried or seen it, that are not being paid by Microsoft. And I wanted to share my thoughts on it after I tested it. In the past I have used WMP v8/9, before using iTunes 4. I loved iTunes so much, that I decided to buy an iPod and loved it. So iTunes sold me on the iPod, and not the other way around. For the record I run iTunes 7 on Windows, I own 8 iPod (Various Models, I don't like to get rid of them after I upgrade), and I buy most of my music (and TV Shows) of iTunes (much cheaper than buying a CD for 1 song). I have roughly 4,000 songs, 1,400 TV Shows, and 15 movies from iTunes, so I am a heavy iTunes user. I own a MacMini (PowerPC) and like it, so I have nothing against apple, but I am more of a windows user and that won't change anytime soon. I do not like the Zune Player, it is a cheap imitation. But I do have to admit I like the new GUI somewhat. The Zune GUI is little too graphical, and the iPod not enough. The perfect balance would be somewhere in between the 2 GUIs. I downloaded and install Zune Software yesterday, here are my impressions. 1) The main thing that attracted me to the iTunes was the light DRM model they used, compared to WMP. iTunes allows 5 machine, 7 burns, deactivation, very liberal compared to WMP which usually was 3 machines and 1 burn. I did a test when iTunes came out for Windows, I bought 10 songs from iTunes and 10 from Buy.com (a WMP site). I can still play the 10 songs from iTunes, but the Windows media version are long gone (money down the toilet due to the DRM)(and yes I can rip it from the CD but that doesn't count ). Zune has copied the itunes DRM model, which is good. 2) What is not so good is that they used WMP as the basis for the Zune Software. It is very difficult to navigate, editing the tags is more a pain in the rear then in iTunes, they are MUCH more tags to choose from, but really who has the time to edit that many tags? And some of the best tags are missing such as Skip Count and Last Skip Date (these are new to iTunes 7, and ARE really useful). 3) It adds AAC support , you can take unprotected iTunes file an add them to the Zune Library and it reads all the tags and plays it perfectly (good). 4) NO SMART PLAYLISTS ('nuff said) 5) The Store was very badly designed. The layout stinks, It is difficult to find music when compared to iTunes. 6) I did like that the had a section for top Artist in the store, it is interest to see which artist has sold the most music . 7) The points system SUCKS, it is pretty straight forward for a song purchase 79 pts = $0.99. But where it really gets annoying and confusing is for an album or playlist ~ 12,560 for a 16 song playlist, when I first saw that I freaked I thought it was really expensive, but then realized it I needed a calculator to figure it out how much the playlist really costs (roughly $16). VERY, VERY confusing, I like the iTunes model better. 8) No TV Shows, No Podcasts, No Movies. 9) Decent Selection, some stuff on there that iTunes doesn't have. 10) No CD-Text on burns, no sharing between PCs only X-box. 11) Registration VERY complex, you need a X-Box live handle, and a Windows Live ID. And unlike iTunes, you are required to do it before you can browse the store. 12) Previews are only 30 secs, I had read somewhere you could preview a song completely in the store 3 times but that was a lie. 13) Files in the store are 128 WMA, same bitrate as iTunes. 14) The one thing that REALLY impressed me was the "Restore Library" function in the account page. It will scan your library and your purchase history and show you what you are missing and lets you re-download it for free ! This is really a GOOD thing, a lot people say it is your responsibility to backup, and not Apple's but they are WRONG. this is the digital age you should be able to re-download your music ALL you want. I know the argument if you buy a CD you can't go to BestBuy and get a new one, but this is DIGITAL. And are much more likely prune to failure than CDs. I make good backups, but I have occasionally lost a couple of file here and there. There are saving a ton of money by not putting it on media, so why not give you free re-downloads ? And when you have about 500GBs of TV Shows, it does start to become a bit of a challenge to back up. Over all, I found the Zune Software very immature. I cannot say I was disappoint because I was not expecting much . I am not a big fan of MS, but this Zune is a multi year thing and they can hurt Apple if they got rid of the point thing and beef up the software and hardware. Because, yes it was bad but this is just version 1. To be honest I dislike MS attitude of having to have it's hand in everything, but with time (maybe around v3) they might actually catchup with Apple. And if they are giving people everything iTunes does (same DRM, similar software) plus stuff iTunes refuses (free re-downloads, and subscription). Apple could be in trouble, hopefully they will adopt fast (copy all the good thing MS has) and keep ahead (by innovating) of MS.