More than one computer iTunes sync

     I recently upgraded to a newer model of macbook pro.  My old one was 4 months too old to sync at all with my Iphone 5 (which is frustrating in itself).  When I'd gotten my iphone 5, I first synced it to my family's mac and transfered much of my music from that itunes library. 
     When my new laptop arrived and all software was fully updated (itunes 11.1.3, and ios 7.0.3 on the phone),  I was unable to sync my phone with the new macbook pro.  I can access my phone from Itunes, but when I would try to add music to it from my library, the device would not highlight blue like it normally does to accept the media.  When I connect the phone to my family computer the box saying "Manually manage music and videos" is checked, but that same box is not checked on my personal computer.  When I try to check that box, a prompt saying: "The iPhone “X” is synced with another iTunes library on “XYZ's_MacBook Pro”. Do you want to erase this iPhone and sync with this iTunes library?  I wanted to avoid this.  Both Itunes libraries are connected to the same itunes account.  Arent we allowed to connect each device to up to 5 separate computers? Both of these are connected to me and my family, the music belongs to me, it's not like I'm trying to steal hundreds of songs from friends.  I spent 2.5 hours on the phone with apple support.  No solution or difinitive answer.
I finally agreed to "erase and sync"  Then I could drag and drop music from my personal library to my phone.  But when I tried to recollect the music from my family computer, I had the same problem as from the start. 
Am I losing my mind? Or is this just a money grab on apple's part? I definitely used to be able to collect music from my family computer as well as my own.  They should not be mutually exclusive.  I am in tears from frustration.  Please help. 

Sync iPod/iPad/iPhone with two computers
Although it isn't possible to sync an Apple device with two different libraries it is possible to sync with the same logical library from multiple computers. Each library has an internal ID and when iTunes connects to your iPod/iPad/iPhone it compares the local ID with the one the device normally syncs with. If they are the same you can go ahead and sync...
I have my library cloned to a small 1Tb USB drive which I can take between home & work. At either location I use SyncToy 2.1 to update the local copy with the external drive. Mac users should be able to find similar tools. I can open either of the local libraries or the one on the external drive and update the media content of my iPhone. The slight exception is Photos which normally connects to a specific folder on a specific machine, although that can easily be remapped to the current library if you create a "Photos" folder inside the iTunes Media folder so that syncing the iTunes folders keeps this up to date as well. I periodically sweep my library for new files & orphans withiTunes Folder Watch just in case I make changes at one location but then overwrite the library with a newer copy from the other. Again Mac users should be able to find similar tools.
As long as your media is organised within an iTunes Music or Tunes Media folder, in turn held inside the main iTunes folder that has your library files (whether or not you let iTunes keep the media folder organised) each library can access items at the same relative path from the library folder so the library can be at different drives/paths on different machines. This solution ensures I always have adequate backups of my library and I can update my devices whenever I can connect to the same build of iTunes.
When working with an iPhone earlier builds of iTunes would remove any file not physically present in the local library, even if there was an entry for it, making manual management practically redundant on the iPhone. This behaviour has been changed but it will still only permit manual management with a library that has the correct internal ID. If you don't want to sync your library between machines on a regular basis just copy the iTunes Library.itl file from the current "home" machine to any other you want to use, then clean out the library entires and import the local content you have on that box.
tt2

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