What's the best way to transfer ALL existing content to new iPhone?

Question

Because "Backup" and "Restore from Backup" have not worked for me in the past. I don't want to have to re-create all of my existing app data - passwords, logins, game progress, etc. I'm not worried about email and contacts, as those are easily synced from Google - but losing the rest of my data again after "Backup and Restore" operations has me nervous about upgrading to 4s.

Answer 1

Jay Kappmeier wrote:
Whenever I bought something directly from the iPhone in the past, the next time I went to syc it to iTunes a dialog box popped up asking me if I wanted to tranfer items purchased on the iPhone but not in the library.  
Jay
Yes, but I think the process is different between auto-syncing an iPhone and manually managing an iPhone.
If you auto-sync your iPhone you'll be prompted about purchases on your device which do not yet exist in your iTunes library. You would normally choose to transfer these purchases, then the auto-sync proceeds as usual and a backup of your iPhone is made with each auto-sync.
If you manually manage the iPhone's contents, just connecting it to iTunes may not automatically initiate these processes. If you just want to drag and drop a playlist from your library to the iPhone, purchases may not be transferred and a backup may not be created. But if you click the Sync button then these two things do happen. If you don't have any new purchases on the iPhone, you can either click Sync or Create Backup to just create a backup of the iPhone.