Hello! Unfortunately nobody can "contact you" (send you a message) until you have contacted first, so the initial questions will have to be laid out right here in the bid proposal.
There's just one "major" question, of which I am suspecting you have not thought of. That is, assuming that point (2) functionality is aimed at the new image uploads through the media library, then there would be a disambiguation when the code has to determine the upload directory - because:
1) The new image might be uploaded from within the edit screen of an existing (old) post, in which case, upon saving the post the (1) function is to be applied, if the image is attached with the post, so at first the upload directory will have to follow (2) and immediately after that (2) which means that the image itself will have to be moved, physically, between the two directories as well, otherwise it will end as 404 on the post
2) An image, previously uploaded in media library, but not attached to any post, is attached to a post - then it will have to be moved to a directory following (2) upon saving the post
3) It's not quite clear that (1) path has to follow the usual wp upload path or the one calculated as per (2). If the latter then parts of the above would no longer be true, especially in point (1), but not the physical moving of the file.
4) I am assuming that (1) is to be a function to apply this to all existing posts (how will be determined which exactly?) at once without actually editing them.