Fastdude wrote:
"He will have to transfer all content into iTunes from the iPad before he can sync with iTunes."
I thought iTunes automatically and immediately starts to sync when an iPad/iPhone is connected? Will iTunes allow me to transfer content before syncing?
You will have to transfer the content into iTunes or when you sync, iTunes will replace the content on his iPad with the contents in his new empty iTunes library. Since it will be a brand new iTunes library on your Mac, the library will be devoid of all content so that will erase the device. You will get a message stating that will happen if you try to sync without transferring the content.
The good news is that it is very easy to transfer content that was purchased or downloaded in the iStores on the iPad into a new iTunes library. I would suggest turning off auto sync before you even hook his iPad up to the Mac. This is also very easy to do. When you set up his own user account or his own iTunes library, launch iTunes (don't connect the iPad) and go to iTunes>Preferences>Devices. Click on the box at the bottom of the window that says Prevent iPods, iPhones and iPads from syncing automatically. Then click OK and you can quit iTunes.
When you turn off auto sync, you will have to launch iTunes now when you connect the iPad, because it doesn't start up on its own when you disable auto sync. I have had iOS devices for years and have never used auto sync. I want to control the sync myself in case I want to make changes which I quite often do.
Now connect the iPad to your Mac, launch iTunes and follow these instructions.
Redownload or transfer your iTunes Store purchases from an iPhone, iPad or iPod to a computer - Apple Support
If you somehow make a mistake or of all of the content isn't transferred, remember that you can download purchased content again as long as you use the same Apple ID that was used to make the purchase. That is also explained in the support article.
After you transfer the content, the next thing to do would be to make a backup. This is very easy to do as well.
How to back up your devices using iCloud or iTunes - Apple Support
Once you you have backed up, you should be good to go. If you want to turn auto syncing back on again, just follow the steps that I posted above but remove the check mark from the box next to Prevent iPods, iPhones ...etc.