Chunk uploading files via WiFi with Espressif boards

Derived from this FS2 Camera project I would like to make an sequential uploader that matches this use-case.
Any file major than 50 Kilobytes will be uploaded in chunks of 50 Kb, using the following workflow:

Picture.jpg (150 Kb) -> Read fifo from Arducam
                                              -> Send first 50 Kb to upload API along with an md5 hash of this first 50 Kb (Called API from now on)

API uploads this first 50 Kb chunk and returns a true if md5(File)==hash received if not returns false

-> ESP board receives this signal and repeats the upload if it’s false up to N times (3 or 4 times at least)

When sending the last part to API, we will add some parameter like EOF = 1 or something in this direction so the API understand this will be the last part to receive. And in successful upload of this last part the server side API will put this chunks together and return the full URL to the image.

This can be the basis to upload big images with consistency.

As you can see here uploading any File that is larger than 40 / 50 Kb is already a big challenge.  And I still didn’t saw this implemented anywhere so it will be a great challenge to build something in this direction