Wireless sync works only partially

I'm running IOS 5 on an iPhone 3GS. I have wireless syncing set up and have followed the instructions carefully, at least I think so. The problem is that I want to sync only one playlist from iTunes onto the iPhone. The name of the playlist does indeed sync, but the playlist is empty on the phone. The computer in the equation is a black MacBook running OS 10.6.8.
By the way, the sync method I am using is to have Sync Music checked on the device's music tab, and I have a check by the playlist I want to sync. Is this not the correct method?
One more piece of information to add. I just noticed that in iTunes, when I click on the device, I do see the playlist listed there, just like it is on the phone, but all the songs on the playlist do show up in the iTunes screen, but they are greyed out. I am totally confused.
Any help would be very appreciated.
Thanks,
Ben

I'm having a similar problem.
Running Snow Leopard on my MacBook Pro, and with a new iphone 4S: I have wifi sync enabled, and it goes through the steps, but after it does a wifi sync the new podcasts that were just transferred to the iphone appear as grayed-out titles only. They don't really transfer over.
Any help on this? I hope I don't have to upgrade to Lion, since my MBP is too old to do that. But this is also supposed to work on Windows machines, right?

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