The 10 minute limit is in part a measure to prevent against DOS attacks to 
the upload url that is generated.

The scenario you have described is usually handled by using some javascript 
to create the upload URL on demand when the user is ready to submit the 
form.

Work is being undertaken to provide a more descriptive error rather than 
just redirecting to the temporary blobstore error URL.

You could probably 
star http://code.google.com/p/googleappengine/issues/detail?id=6313 if 
being able to redirect to a specific URL on upload failures as well.

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