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I have fairly actively avoided Apple products most of my life so diving into a Macbook/iPhone setup has been quite an experience.

First of all, I really like the iPhone 3GS.  I was really hoping that the Android platform would become a serious competitor to the iPhone but so far, it really hasn't so I've decided on the iPhone.  I haven't been disappointed by much on the iPhone.  The web browsing experience is fairly fast and usable.  This is a great improvement from Virgin Mobile's poky mobile browser on the LG Rumour that I had been using.

One of my biggest concerns was the need to use iTunes.  Past experiences with it have not been positive to the point that we've joked that the Windows version should be caught by anti-virus programs as a virus.  Now that I've got a Mac, I figured that iTunes should be a well integrated and highly functional part of the environment.  Sadly, iTunes seems to be as poorly written on OS X as it is on Windows.  I have not had so many problems with a mature piece of software from a major developer in my 30 years using and developing software for computers. 

My first adventure with iTunes was getting a library of 7000 songs onto the iPhone.  That would seem easy to do.  Import the files across the network from their repository on a Windows server.  I do this every time I install a media player, usually WinAmp, on any other computer on the network.  It generally tasks under an hour to go through the files, get the ID3 tags and build a database of songs.  So I started the process with the iTunes "Add to library" function.  It would have been nice to just enter the UNC path to the song archive but no, I had to use the finder to map a "disk" to the that location on the network and then access my songs from there.  Lots of mousing around where a few keystrokes should have done it. 

So the import began.  After a couple of hours, I realized that this was not going to be a quick process.  Not only that but the computer was completely unusable while iTunes with in this import process.  So I left it until the next morning.  Well it was "done" but it had only imported about half of the songs.  It looked like the network connection to the share where the files were located had "gone away".  The machine was on a wired connection to a rock solid network and server.  Not sure what went wrong but I started the process again.  Many hours went by and this time it looked like iTunes could see all of the songs.  They played well.

I was ready to start putting music on my new iPhone.  It was about 3 days old at that point and I had not been able to get any music on it.  So I started to sync with the iPhone.  I left it for awhile.  When I came back only about 500 songs had sync'd.  Why only those songs?  They all seemed to be songs that had poor ID3 information in them.  Maybe iTunes hadn't imported the songs well so I remove all the songs and started importing again.  Another night went by.  Next day, the iPhone sync seemed to import the same 500 songs only.

One thing that stuck me was that maybe iTunes didn't like it that I had imported songs but had told it to leave those songs on the network and not copy them to the Macbook.  So, remove all the songs out of iTunes, and start yet another import with copying of the songs.  Before I did that, I imported a small subsection of the music library and it seemed to get onto the iPhone without any problems.  The big import took about 2 days but when it was done, I was finally able to get my music on the iPhone.  Why this would not work well over the network, I have no idea.

Next task: figure what the "Apple Way" is with respect to podcasts.  Arg!