1. That's the "01" clasp, signifying eligibility for the "South Africa 1901" clasp.
2. Shackleton has most likely put in a claim for the "Orange Free State" clasp as well, which has been rejected
3. Further research would be needed - I didn't see any mention of such in my perusals, but didn't read any Shackleton-specific accounts either.
4. Two great errors at least on my part - Shackleton was promoted lieutenant in 1900, not 1901, and the donkey race also occurred in 1900. Whether that means he had already been in South Africa and had temporarily returned, or had not yet gone out, I'm not sure. My source for the donkey race is the Belfast News-Letter, page 3, 12 October 1900:
"On the 2nd inst. the regimental sports of the 3rd Battalion Royal Irish Fusiliers took place at Richmond Barracks, Dublin, where the battalion is now stationed. The weather was not all that could be desired, as frequent showers interrupted the proceedings, but the entries were large and the prize list a long one. About 150 invitations were issued by officers, and a large number of guests were entertained by the sergeants...proved great amusement, as well as the officers' donkey race, in which event Second-Lieutenant Shackleton won on the post from Second-Lieutenant O'Farrell by a short head."