Freeing HD space from iTunes without losing content during Sync with iPhone

Hey, Y'all!
This is probably a common question — but I had some trouble finding a specific answer by a few attempts at searching. So please forgive any redundancy...
I desperately need to free HD capacity on my MacBook Pro, and parts of my iTunes Library would make good candidates. The entire home/Music folder is already backed-up to an ext. HD (more than 1x).
But I'd prefer to NOT lose whatever I delete from my MacBook Pro's HD when I sync with my iPhone 3Gs and my son's iPod Touch. Both devices have plenty of capacity for what they're holding currently.
How do I set up sync parameters to accomplish this using, e.g., the Music and Videos tabs in the iTunes interface with these devices? And when — do I alter these settings "before" doing the removals from my HD? The answers may be obvious, but unfortunately not to me.
Hope I've made sense in stating my questions. I'm using iTunes 8.2.1 (6) if that's a factor in this...
Thanks for your help!

I finally found several errors that may all help you who may have the same problem. While each of these steps may or many not help you, here is what I did to achieve a resolution. I will provide the logic as much as I can.
1. The problem is as above, unchange
Step 1: I made sure that my Mac (late 2008 unibody, running Mac OS X 10.8.2 with all recent updates) was infact working well. I verified and repaired permissions as well as verified and repaired my HD.
Step 2: I went through my iTunes app library and eliminated duplicates as well as apps that 'hung' (apps that would be updated but never leave the update screen- somehow these apps are duplicated- delete one of these to clean up your app update screen.
Step 3: Check for operating mode. You most likely need to run iTunes 11 on Mac OS X Mountain Lion (and possibly Lion) in 64 bit mode. Close iTunes and open your Applications folder. There select iTunes 11 and under the file menu- select Get info. See if your iTunes is running in 32 bit mode*. Uncheck this if 32 bit mode is selected. Close the window and restart Itunes. Try synching with your iPhone or Ipod (touch). This may work.
*Step 4: If you have 32 bit mode checked, think back to if you installed 3rd party plugins. I realized I have a legacy plugin for iToner that forced iTunes 11 to jump back from 32 bit and 64 bit modes. Check your iTunes plugins and either delete or backup/delete plugins.
After doing all this, my iTunes 11 and iPhone 5 started synching again.
I hope this helps. Whenever there are problems in upgrades, check 3rd party plugins! Check that folder to jog your memory!

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Can no longer download itunes music. Says all content will be lost. No longer on original computer. Is there any way I can download from itunes without losing content.

I can no longer download from itunes on ipod. It is not original computer and new computer message from itunes is I will lose all content on ipod if I continue to download. Is there anyway around this? Also have not updated ipod, is that important.
Arlene

You can transfer you iTunes purchases to your new computer by:
iTunes Store: Transferring purchases from your iPhone, iPad, or iPod to a computer
You can only sync to one computer/iTunes library. You can manage music amond different computers by:
Using iPhone, iPad, or iPod with multiple computers
If you wnat to make the new computer your syncing computer you must restore the iPod.
- See if you can make a backup of the iPod on the new computer by right clicking on the iPod in iTunes and select backup. If successsful, restore the iPod from that backup after tansfering your iTunes purchases to the new computer.
- If you can't make a backup copy/move the backup file from the old computer, That file is located:
Mac: ~/Library/Application Support/MobileSync/Backup/
Windows XP: \Documents and Settings\(username)\Application Data\Apple Computer\MobileSync\Backup\
Windows Vista and Windows 7: \Users\(username)\AppData\Roaming\Apple Computer\MobileSync\Backup\
You may have to turn off hide hidden files.
If you do not have the backup file you have to restore the iPod to factory defaults/new iPod and sync your stuff to the iPod. You will loss all your app data.

How do I delete songs from Itunes without losing them in my IPOD?

How do I delete songs from Itunes without losing them in my IPOD? I don't want 11gb of music stored on my computer when I already have it in my Ipod. Anyone have some info?

You can Transfer music manually, then delete the files from the PC without having it sync to the iPod.
HOWEVER.....
Deleting songs off of iTunes or your computer is a very bad idea unless you have created one or more backup files of all your songs.
Using the iPod as the sole repository of any of your songs is a very risky practice. When (not ‘if’) you need to restore the iPod, return the iPod for service, or it's song files are somehow lost or damaged, you will be re-ripping all your CDs back into iTunes and re-purchasing all your iTMS songs. Restoring the iPod is a common ‘fix’ to many small issues that arise.
If you cannot store your songs on a PC or within iTunes, then you will need to have some storage medium in use (an external hard drive, DVDs or CDs). You should also consider a secondary backup medium for additional safety. Whether you keep your music in iTunes or on an external source – Multiple copies of your music files are a must!
The iPod is really designed to be playback device - not a primary storage device (although it can be used as such), and certainly not as the only storage medium for all your music.
Always backup your PC files: both music and data. Backup as frequently as possible. The usual ‘metric’ is to determine just how much work (hours, days, weeks) or money spent you are willing to repeat by extending out your time between backups. Your choice, your potential headache &/or loss.
Many data-savvy folks have more than one backup and create incremental backups every time they add to or change their Library. Depending on the work I am doing, I may perform several backups during the same day. As they are incremental, and placed on my Backup ExHD – it is a very quick operation to perform several times a day, when needed.
If you are heavily invested in your Library data (Playlists, Play Counts, Ratings, Last Played, Date Added, etc.), then:
it is critical that you also make multiple backups of your ‘iTunes Library.itl’ file.
iTMS REMINDER: While you can always take the time to re-rip the CDs you own to restore your iTunes music, if you lose your iTMS purchased music and have no backups, you will have to re-purchase them. Few exceptions are made to this rule – at least none that I am aware of.
Here is a post on developing a backup strategy:
http://discussions.apple.com/click.jspa?searchID=-1&messageID=1498152

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https://discussions.apple.com/message/23071575#23071575

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When you sync the iPad 1 to iTunes it should copy all of the items from the iPad into iTunes.
However, you can connect your iPad 1 to your computer, launch iTunes, right click on the device name on the left side of iTunes and select Transfer Purchases. This will transfer all paid apps, movies, music etc into iTunes. The you can sync the iPad 1 to iTunes one last time to make sure all content is backed up.
This talks about transferring purchases.
http://support.apple.com/kb/ht1848
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Message was edited by: Demo

If I backup my iPhone to iCloud, can I restore it without losing data after syncing with new computer/iTunes?

The laptop my phone was synced to broke, so I had up get a new computer. I know that if I try to sync my iPhone 4 (running iOS 6) to the new iTunes on the new computer I'll lose my data. I have everything backed up to iCloud. Could I restore my iPhone after syncing with the new iTunes?

yes

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There was another post that said when you change the email address for your iTunes account the Apple/iTunes ID you enter to login is still the original email address.

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When trying to sync apps my Itunes 11 crashes (in the 7/7 phase of synching). When I install from the Itunes app store, no crashing for the app. I had Itunes 10.7.2 and it did not crash.
When I de-select the apps from my library to be removed, all other content syncs well. It seems that apps stored on my Mac do not sync and cause Itunes 11 to crash.
After eliminating other possibilities, it appears that Itunes 11 has a bug. This begs for a fix (11.1) very soon. I will have to do app updates through my Iphone 5 until this fix is made.
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I finally found several errors that may all help you who may have the same problem. While each of these steps may or many not help you, here is what I did to achieve a resolution. I will provide the logic as much as I can.
1. The problem is as above, unchange
Step 1: I made sure that my Mac (late 2008 unibody, running Mac OS X 10.8.2 with all recent updates) was infact working well. I verified and repaired permissions as well as verified and repaired my HD.
Step 2: I went through my iTunes app library and eliminated duplicates as well as apps that 'hung' (apps that would be updated but never leave the update screen- somehow these apps are duplicated- delete one of these to clean up your app update screen.
Step 3: Check for operating mode. You most likely need to run iTunes 11 on Mac OS X Mountain Lion (and possibly Lion) in 64 bit mode. Close iTunes and open your Applications folder. There select iTunes 11 and under the file menu- select Get info. See if your iTunes is running in 32 bit mode*. Uncheck this if 32 bit mode is selected. Close the window and restart Itunes. Try synching with your iPhone or Ipod (touch). This may work.
*Step 4: If you have 32 bit mode checked, think back to if you installed 3rd party plugins. I realized I have a legacy plugin for iToner that forced iTunes 11 to jump back from 32 bit and 64 bit modes. Check your iTunes plugins and either delete or backup/delete plugins.
After doing all this, my iTunes 11 and iPhone 5 started synching again.
I hope this helps. Whenever there are problems in upgrades, check 3rd party plugins! Check that folder to jog your memory!

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A SOLUTION ONLY FOR GURU (Mac experts)
I use Mac OS X 10.7.5 Lion and iTunes 11.1.4 (62) ad making exactly that Apple suggested for Mac OS X 10.6 here: http://support.apple.com/kb/TS3540?viewlocale=en_US
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Hello robertfromphilomath,
Are you having trouble syncing with Microsoft Outlook or with your calendar on iCloud.com? The resource below will provide some preliminary troubleshooting steps:
Troubleshooting Sync Services on Windows with Microsoft Outlook 2003, Outlook 2007, or Outlook 2010 - Apple Support
https://support.apple.com/en-gb/HT203300
If you're having difficulty syncing your contacts or calendars to iPhone, iPad, or iPod touch with iTunes for Windows via USB, this article can help.
If you are using iCloud to keep your content up to date between your iOS devices, iCloud.com, and your computer, please see these articles instead:
iCloud: Troubleshooting iCloud Calendar
Regards,
Judy

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Freeing HD space from iTunes without losing content during Sync with iPhone

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