Want to delete an application and reload it fresh

No matter what, I can remove an application 100% from my Mac and from my iPhone but my itunes account still keeps the record of my download of it. I want to totally remove a free application and just start from scratch but that is not possible, It will always come back with "you have already purchased this item, to download it again for free, select OK". We'll the app was free to begin with and I want to start the whole thing over with no record of having it before. It is obviously tied to my iTunes account, so does anyone know how to clear this? I do not understand this feature, I have had many songs wiped out because they were not backed up yet but those still had to be purchased again. Why is it different for apps? Anyhow, I need to know how to "clear" applications from my account. Can this be done?

One thing that might help out.
The record of you downloading the application is kept in your purchase history.
There is not a way to remove this from your record.
The reason for this is if you lost an application from your iphone and from itunes, you can download it again with out having to pay for it again.
Once you delete the application from the iphone and from itunes, you download it again as a fresh start. You just don't have to pay for it again.
Hope this helps.

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