Itunes on macbook pro looses sync'd content when reconnected

I'm having an issue where I have all my music and movies playing just fine on my MacBook Pro, and the next time I sync my iPhone, any movies or music selected to sync that are not on my computer's hard drive recieve a circle with a bang in it and can't be sync'd. They will sync only after I attempt to play them again on the laptop and the circle with a bang goes away. This refreshing process can get quite a pain and take a long time if I have muck selected to sync with my phone. I have the movies stored on a network drive that is readily accessible whenever my MacBook Pro is at home which is almost always. I am running the latest version of iTunes and have OSX 10.7. Any suggestions other than installing a terabyte drive to move my moves to?

I've had this problem for ages, only now it seems as though iTunes is no longer restoring my music folder to the NAS if I start it when the NAS is connected. This is proving a pain in the a** because I keep forgetting about it, going online and buying a load of music from the store and then I find I've got a gig to consolidate when I realise my music folder has filled up! Funnily enough, I've downloaded and edited an applescript that automatically checks every half hour whether or not I'm on my home network, if I am it mounts my network drive for me. I really miss the airport disk utility's automatic mount feature. What I think I'l do is create another one for iTunes, to serve as a shortcut to iTunes, but when it's run it will check to see if you're on your home network, if so mount the NAS (if it isn't already), if not, or if it can't mount it will ask you whether you want to run iTunes after warning you that your NAS isn't connected. The only potential problem I could see is when iTunes runs as a result of you opening a music file in Finder. However I'm sure we could associate the applescript 'shortcut' with music instead of iTunes? I'll post here if and when I'm successful.

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    Hi there!
    I suspect I know the answer to this already, but I hope I'm wrong! :-D
    I have my macbook a while now, but I've only recently started using iTunes properly.
    I have a home network, which consists of my macbook pro, a dell laptop running XP, a Nintendo Wii, a Sumvision Netbox NAS 1TB drive and a Logitech Squeezebox Boom.
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    The Squeezebox Boom (for anyone who doesn't know) is a neat little Wifi radio/mp3 player, it streams radio from the web, and also music from the NAS.
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    At the moment I have this software linked to iTunes, so when I add music to my library via iTunes the squeeze center automatically scans the music library and updates itself taking in music details, play lists, art work and all, it's a great system.
    The problem I have is when I take my laptop anywhere, iTunes changes the iTunes music folder location automatically to the internal hard drive, which means when I get home again I have to reset the file path and iTunes then has to scan the folder and organise everything again.
    not only that, as soon as the squeeze center sees the file path has changed it points at the new location (on the macbook hard drive) and looses the library.
    so when I reset iTunes, the squeeze center has to rescan everything again also.
    It's quite annoying.
    I have a work around in that I can tell the squeezecenter not to look at iTunes and hard wire it to the location, but I'd rather not do that.
    Is it possible to get iTunes to keep the NAS music folder as the iTunes Music folder location even when the macbook isn't on the network?
    Or will it always change the folder when I leave the network.
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    I've had this problem for ages, only now it seems as though iTunes is no longer restoring my music folder to the NAS if I start it when the NAS is connected. This is proving a pain in the a** because I keep forgetting about it, going online and buying a load of music from the store and then I find I've got a gig to consolidate when I realise my music folder has filled up! Funnily enough, I've downloaded and edited an applescript that automatically checks every half hour whether or not I'm on my home network, if I am it mounts my network drive for me. I really miss the airport disk utility's automatic mount feature. What I think I'l do is create another one for iTunes, to serve as a shortcut to iTunes, but when it's run it will check to see if you're on your home network, if so mount the NAS (if it isn't already), if not, or if it can't mount it will ask you whether you want to run iTunes after warning you that your NAS isn't connected. The only potential problem I could see is when iTunes runs as a result of you opening a music file in Finder. However I'm sure we could associate the applescript 'shortcut' with music instead of iTunes? I'll post here if and when I'm successful.

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    Everything is updated!!  iPhone, iPad, iTunes and MacBook Pro...  All I am trying to do is drag content from my iTunes Library to the devices.  iTunes gets stuck EVERY single time!  What usually triggers the Non-Sense is when I am adding a 2nd file!
    Why does iTunes SUCK??
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    I used to be able to drag over 1000 tunes, movies, etc. go have breakfast come back and it would all be on my device!!
    Can't do it anymore, one song at a time, maybe an album at a time, or one movie, and that is it!!
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