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I know that pages which are redirected will not index well, so I am planning on submitting the actual url where the content is located.
My set-up: I have the website logo with a link to the masked url which links to almost the same content. I then have a text link below it which links to the actual page of the content.
My Question: Will having the image linking to the masked url hurt the overall indexing of the page as the two links ultimately point to similar content?
However, you may have a problem dealing with the PageRank as the distributed domain / IP / content may not capture the parent PR value for the domain.
You may want to re-think for a long-term startegy