iPhone + iTunes syncing set up is about as plug and play as you can get. Install iTunes. Plug in the iPhone. You're in business. Unless, like me, your primary OS at home in Linux. There are more drivers for it these days, but when I first got my iPhone, linux just would not see that it existed. (Frotunatly I have a Windows XP box as well, so thats been my primary music box. For the benefit of a fair comparison, I'm going to try to sync things to the same XP box)
So, first things first, I plugged the phone into my computer. By default it seemed to go into charge mode only so I had to tell it to mount itself as a drive. This is slightly annoying default behaviour, but I'll bet there's a config option somewhere to stop that.
The first thing I notice is that there's some HTC Sync software on the phone. So I decide to install it to see what it's about. Maybe that'll help me get music on there. It installs (after telling me to turn off any virus checkers I might have running (eek)) and runs. I'm barking up the wrong tree here. This is only for syncing contacts it seems. Not very useful, so I decide to Google for music syncing for Android. The result of which is an install of the doubleTwist software.
It seems really cool if you use iTunes (which I will continue to do on account of there being three iPods of various description in the house). It inspects your iTunes library and uses that to work as a sort of iTunes for Android. Cool!
The first problem is the size of my collection. I have 21,000+ tracks in my collection. The inital scan of the iTunes files takes about 4 hours. The next problem (and some would argue a more fundamental one) is that it totally fails to detect my plugged in phone. It appears to have created a .doubleTwist directory on the phone, but that's it. It still says that it can't see the phone. I'm a couple of beers into the evening and getting a little annoyed at this point. Things shouldn't be this hard. I am reminded on Linux vs Windows. Linux is a much better OS, but WIndows will always be more popular because (even with all this bugs) 'works' with not too much hassle. Time for plan B... Media Monkey.
I'm hoping that Media Monkey is to Windows what Amarok is to Linux. I am make the switch away from iTunes if this tunes out to be a closer fit for my needs. It can sync to Apple gear. At this point I thought I would take a break as I left Media Monkey to index my entire music collection...