2. What good does it do to have an order "in writing" when "in writing" means "electronically on a PADD"? Is there anything to keep that electronic copy from mysteriously being deleted next time Starfleet starts asking questions?
We still say we 'Dial a number' even though telephones have not had dials for decades. I would suppose official records are kept in an audited file. Whenever it's accessed, it's specifically recorded who accessed it and what they did. Sure it's possible to get around security protocols and delete, particularly if Mister Garak is your friend, but Bashir would not expect Sisko to throw him legally under the bus. He just wants an official record that he is not legally responsible. Sisko probably could have said 'No, just give me this' and Bashir would have backed down, but Bashir was leaning on their friendship when he made that request.