Question: best path to sync iPhone with MacBook (Entourage or Mail)

Question

OK-
Have been putting this off for some time. I have an iPhone that I used to sync with my WinXP laptop. I replaced the laptop with a new MacBook Pro and need to do (2) things:
1.) Migrate my contacts over to the MacBook
2.) Determine my long-term contact/calendar/etc. sync plan
1.) Migrate: are there any good tips/threads out there for how to do this? Since my iPhone is the only place these reside currently and iTunes wants to bi-directional sync when I first connect... I'm nervous about this! What's the best way to make sure I can successfully get my contacts onto my Mac from the iPhone without losing them?
2.) Syncing: I'm currently using Entourage:Mac 2008. I've read thread after thread about problems syncing between iPhone and Entourage... I understand it to be primarily because of reliance on Address Book and iCal as intermediaries, correct? I wish I could say I could switch to those but the integration of Entourage with calendar, contacts, tasks, etc. is just too useful for my work.
So - any suggestions, pointers, even added utilities, that will help me set this up to work reliably would be much appreciated.
Also - one thought has been to use Google Apps to sync mail, contacts, and calendar. However, I'm not a fan of how GMail accepts every email address as a contact...
At any rate, I'm looking for pointers on any of these fronts. Any guidance would be great!
Thanks,
- JBro

Answer 1

1.) Migrate: are there any good tips/threads out there for how to do this? Since my iPhone is the only place these reside currently and iTunes wants to bi-directional sync when I first connect... I'm nervous about this! What's the best way to make sure I can successfully get my contacts onto my Mac from the iPhone without losing them?
I suggest using Apple's Address Book application for storing contact information. If you decide to use Entourage for email account access, contact information, and calendar events, Entourage syncs with Apple's Address Book application and with iCal for contact information and calendar events which syncs with the iPhone.
Before syncing, enter one contact in the Address Book application and one calendar event in iCal. Make these up if needed which can be deleted later. This should provide a merge prompt which you want to select. This will transfer all contact information and calendar events from your iPhone to the Address Book and iCal.
2.) Syncing: I'm currently using Entourage:Mac 2008. I've read thread after thread about problems syncing between iPhone and Entourage... I understand it to be primarily because of reliance on Address Book and iCal as intermediaries, correct? I wish I could say I could switch to those but the integration of Entourage with calendar, contacts, tasks, etc. is just too useful for my work.
There can be problems with this, which relies on a sync services feature included with Entourage that syncs Entourage contact information and calendar events with the Address Book and iCal, which are used for syncing with your iPhone. So there is an additional step and sync function when using Entourage.
If you haven't transferred your iTunes library from your PC to your Mac, you should do so. iTunes includes an option to transfer content that was purchased from the iTunes Store from an iPod or iPhone, but this is for content that was purchased from the iTunes Store only. Before syncing, at the iTunes menu bar go to File and select Transfer Purchases From - the name of your iPhone.
For all other iTunes content on your PC that was not purchased from the iTunes Store, you need to transfer this content from your PC to your Mac.