Rob, KC8RCO, sent me an article from the July 2007 issue of Popular Communications in which Bill, N3AVY, proposes to send pictures via CW. CW is the original digital mode after all, isn’t it?
It is an amusing idea. I would suggest, though, that he start with a small image, such as the small ARRL icon. The .ico format uses only 16 colors, meaning that the colors require only four bits, and that each byte contains the information for two pixels.
The ARRL icon is only 766 bytes, meaning he’ll have to send 1,532 characters after encoding the binary data as ASCII. After he’s successfully sent and received the .ico image, then he could move on to something more complex.