ITunes 9 syncing issues

Hei everybody,
I was trying everything myself, I was googling all around, but couldn't find the answer to my problem. So I came here to ask for help.
Ok here is my problem:
My iTunes doesn't normally sync with my iPod. The thing is, I always manually manage my music and videos with both iPod and iPhone. I download podcasts (subscribe) and iTunes U content. Then upload them to my iPod or iPhone. Listen to them and when I reconnect them to my iTunes library and sync them, my iTunes automatically mark the podcast on the mac as watched. At least this used to be with the older iTunes version. Now after updating to iTunes 9, when i connect my ipod and press sync, iTunes does not recognizes, that I have listened to some of the podcasts, and doesn't mark them as watched.
With iPhone i have another problem. iTunes recognizes the podcast that I have watched, and marks them as it should, but now I can't see my iTunes U content on iPhone. If I put something form iTunes U on my iPhone, and in the iPhone it shows, that there is nothing on there..
So do you have any idea why my iPod and iTunes 9 doesn't sync normally?
I have fresh install of Mac OSX 10.6.1, iTunes 9, newly restored iPod nano 3g 4gb silver with 1.1.3 firmware, iPhone 2g 8gb with 3.0.1 OS.
I wonder if the last.fm app for Mac os has anything to do with it?
Thank you!

I'm having the same issue as far as the iTunes U content goes. I have downloaded several video / audio files. Made sure to select them, right click and choose "Make iPod / iPhone version". After syncing (it is properly set up to sync iTunes U content) nothing shows up. Also, if I try downloading the content from iTunes directly on my phone it downloads, but never shows up anywhere.
I'm trying a restore now. Does anyone have any thoughts?

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