Migrating Applications from Windows to Mac with new iPhone

My original first gen iPhone died a horrible death a few months ago. I had always synced it to my Windows laptop. I just recently acquired a new iPhone and want to sync it instead to my iMac. However, I have a dozen or so iPhone applications that I still want and I cannot figure out how to migrate the applications that are recognized by iTunes on my Windows machine and transfer them to my iMac. I even attempted to download an application I already purchased from my iMac, and I was charged the fee for the iPhone application instead of it just recognizing i had previously purchased the application.
Any assistance would be greatly appreciated.

*1) moving the music*
These pages may be of some help:
How to move an iTunes library from a PC to Mac (and back)
How to move your iTunes library from Windows to Mac
*2) restoring the ipod as a Mac device*
Connect the iPod to the Mac and restore it in iTunes. Restoring in iTunes for Mac will erase and reformat the iPod's hard drive, reload the software with the mac version and put it back to default settings. Once the restore is complete follow the on screen instructions to name the iPod and automatically sync your songs and videos onto the fresh installation. Press Done and the iPod will appear in iTunes and start to sync. If you want to update manually or using selected playlists uncheck the box beside the sync automatically instruction and press Done, it will default to manual mode and you can choose whatever setting you like: Restoring iPod to factory settings with iTunes
*3) pointing iTunes to and external library.*
You might find this article useful: iLounge - Managing your iTunes Library on an External Hard Drive

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