I still don't see any syncing going on, though. Finally I decided to simply manually copy the contacts from my main Outlook Contacts to my new Windows Live contacts folder. There are of course duplicates, so I got an alert asking me how to handle those. I directed Outlook to merge the information using my Outlook data as the primary.
Next, as the data was being copied I got alert, after alert, after alert declaring, "The company name exceeds the limit of 40 characters. Type fewer characters before you click OK or excess letters will be automatically removed." The only problem is that it doesn't provide me with any indication which contact is in question, or any means of altering it. I can choose between blindly clicking "OK", or clicking "Cancel", hoping I can figure out which contact is the problem, then starting the copying process over again. I just click OK.
As it finished copying, I got a message stating, "Cannot copy the items. Some items cannot be copied. They were either moved, or deleted, or access was denied." Um, OK. Which contacts? I didn't move or delete anthing mid-copy process, and I should be the only one with access or authority to deny access, so I don't understand what the problem is.
At the bottom is a taunting link asking, "Was this information helpful?". No, Microsoft. No, it was not helpful at all.
It was an arduous and frustrating journey, but my Outlook contacts data is now incorporated with my Windows Live contacts data so it can be synced with my Windows Phone 7 device. As far as I can tell, though, there is no automatic syncing going on. If I add or change a contact in Outlook, I am going to have to manually copy it over, or make the same add or change in the Windows Live contacts in order for that information to get to my phone.
I am sure my experience is not the norm. I did this before and it wasn't this hard. I still thought it was a convoluted pain in the ass, but it wasn't so frustrating just to get it set up in the first place.
That said, Microsoft really needs to automate this entire process. Part of the initial setup of a Windows Phone 7 smartphone should include an automatic query, or asking the user if they use Outlook for contacts and calendar data. If so, Windows Phone 7 should automatically install the Outlook Hotmail Connector or whatever tool is required, and automatically pull that data to Windows Live so it can be propagated to the Windows Phone 7 device.
The information should be able to be synced in the background without cluttering up Outlook with folders from Hotmail. And, most importantly, it should automatically sync all changes made to Outlook. I shouldn't have to be involved in setting up or babysitting the contact info--especially when I am using Microsoft Outlook in the first place.
My iPhone syncs my contacts and calendar from Microsoft Outlook just fine, and doesn't require Tylenol or anger management.