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Yes you can clear uploads anytime you want just do not delete data directory
As far as uploads not working what type of file is this your trying to upload. The error your site is reporting is a GD2 error and usually in those brackets it has a file type but yours is empty. So the result here is to understand why your not getting an error type
You can place a url here and a test login here so we can try uploading
Recheck your uploads and data directory permissions and ensure that they are 777 at every level.
The reason I asked you to clear uploads is because if you by chance uploaded a file not supported by GD2 this could be a reason why your getting stuck on the upload process.
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