Moving music / data from iPhone to iTunes

Hard-drive burned up and has been replaced. Most music was backed up, but not all. And most of the new music (that hasn't been backed-up) is on the iPhone. But I can't copy the files on my iPhone back to my new hard drive. Obviously there are security measures to keep folks from transferring files all over the place. But it seems that if it's on my iPhone, I must have obtained it legally, and there must be some accommodation for a dead hard drive.
Same question for my iPhone apps. I'd rather not pay for apps twice, and iTunes won't let me copy them from my iPhone back onto my 'puter. As soon as I sync apps, they'll all disappear, unless there's some way to convince the phone that it's looking at the old, pre-burned-up-hard-drive.
OS X 10.5.8, iPhone 3G with 3.1.3
Thanks!

File>Transfer Purchases sort of worked, but not completely. I have about 600 songs on my iPhone, and it copied about 200 of them to my new hard drive. I have music purchased from iTunes, music copied from purchased CDs, and free downloads (Starbucks, Paste, etc). And there's no trend in what got copied and what didn't. Some of each category was copied, but not all. Very confusing that I can't find a pattern.

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    even if the search terms or words are changed around quite a bit.
    For just moving iTunes music, that is easier than data; and I can
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    Most of the sync information on how to move stuff, tends to delete
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    Is there a way you could use a gmail account to save and move
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