Not sure about others, but I prefer taking the boom off. I'd take it off before dropping the sail in light winds, but consider leaving it on in strong winds..helps to pull the sail in neatly
With the boat pointing nicely upwind, it drops the sail onto the tramp. It's nice to have the crew sort of loop it in a s shape while coming down, releasing the batten tension at the same time. Then roll, stating from the top keeping the battens parrallel and taking out any wrinkles in the sail at the sides. I take the top of the sail lap it onto the second batten, then roll from there, so the top is tucked in..not sure if this is good practise. But a neatly rolled dry sail is good for storage I think With the boom seperate...