Having trouble syncing Apps download on iPhone 3Gs to computer, HELP?

I have had an iPhone 3G for almost a year now and have downloaded numerous Apps. Some that I have purchased and other that were free. I want to download the new iPhone update and restore my phone but don't want to lose the Apps I purchased. I switched apple accounts about 1/2 a year ago because it was linked to an email that I used in high school and created a professional one for college. Is their any way on identify the account used to download certain Apps and if the email address it may be linked to no longer exists is there anyway to download the App without being charged a second time? The main reason I would like to do this is my HDD crashed and after installing a new one my iPhone no longer recognizes it.

Can you give us the exact error message, please.
Otherwise there could be a thousand different things going on!
In the meantime try the reset if you haven't done that yet (maybe it helps, at least it's quick): press and hold the sleep/wake and home buttons and releasing them, when the Apple logo appears on the display.

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