Transfer Purchased onto iTunes not working

Today, I borrowed my friends iPod to download the purchased songs onto my iTunes. When it said it was finished, it only transferred 34 out of 300 and some odd number purchased. Could you help me please? I authorized the account and clicked on transfer purchases.

I'm pretty sure I remember this working before as well. Now that doesn't work and updating apps on the handset itself doesn't work properly either. As soon as you sync with iTunes though the process completes. Annoying to say the least. I love the fact that I can browse for software will out and about but if I can't transfer it to my library what's the point?
I guess once you have paid for applications, rather than free ones, you could go home and download it again via iTunes and you won't be charged twice?

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