Only ask for Sig if the buyer requests it. I hate it when seller does that to me, im rarely home to catch it and makes the whole thing a worse, longer, drawn out process that adds sometimes days to the drop off.
Always insure, track, priority is good. If you dont care to spend a little extra (easy come easy go, right?) get it there overnight. Hes happy, risk in minimal, transit times are diminished.
Otherwise, just treat it like all the others, just add some insurance.