If in doubt, I'd just do it. It takes a bit of time, but packing is cheap.
On my own boat, I wouldn't hesitate to do shaft packing in the water. Rudder packing I'd only do in water in an emergency. The access sucks (you're basically laying across a fuel tank upside-down in a small space and working mostly blind). And there's barely enough room to get the packing nuts off without dropping the rudders, so it's not quick and easy like shaft packing.
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