Hmm, I didnt know we were talking about the IPhone here, I only assumed that we were discussioning MP3 players and not phones.. maybe I was mistaken...
See a few things to think about... first off I tend to like to keep my things as legal as possible, so I dont do alot of downloading music.. I mean I do.. but why worry about it when I can pay 15 a month and have all the songs I Want.. no worry with sifting through torrent files.. or anything like that...
All my songs are properly labeled with proper genre, artists, and albums... something thats very hard to find in torrented music (or limewire, bearshare, whatever you want to use)
Further more, yes zune will catch up, because making stuff for the zune is about 10 times easier then making it for the ipod.. the closest hting to easy you get with the ipod is using unity3d engine... and thats only good for games. You heard it first guys, 3 years.. zune will win (think of a market that mircosoft competes in and it doesnt have the best... really...more people can argue a few.. but at the end of the day everyone knows microsoft puts out good products.. yeah I said that too)
Iphones are nice... I mean I guess.. I really dont do much with mine anymore.. I prefer my blackberry over my iphone.. might cell it (haha see what I did there with cell.. and sell)
Yeah, you can use playon, or tversity or any of those other programs to stream media through out your house.. but why.. when using an MS product it all just works together? Trust me I have worked with play on and tversity both of them are subpar programs at best, however I Would say playon is defently better most likely why it costs..
Jailbreaking is risk free, pretty easy, and really lets the ipod shine.. but why? I mean why buy something that you have to "jailbreak" to get the features you want.. why not just buy something that is limitless for the future... allows awesome applications to be built easy (check out xna you might learn something too) and regaurdless of what anyone says, or thinks. Will sooner or later take over the mp3 market just like MS takes over every market.
Really you should do your own research, see what you think, and if your already biased about one product then your most likely just going to be looking for excuses to use that one and could careless about the other one.
Zune to date I have heard no crazy horror stories about, and ipod.. well just google. I have owned both and never had any problems with either.. I just felt that the zune.. as I said earlier meshed much cleaner into my life style, from home to on the road there was always a reason to have my zune.. Ipod well.. it sits in my night stand more often then my pocket...