The advantage to deploying them later when you take the sail down is that you don't have to worry about them being to tight and rubbing against the camber of the sail. I have a tiller pilot to hold course into the wind while I deploy and lower the sail. (I say all of this ,but I might decide to do it a different way next month .I fully retract the Jack’s and if I hoist the main while still on the mooring, I will deploy but I often forget and then it’s lock the wheel, run up and do one side, run back, stabilize, run up, do the other side, or bring a kid to do it for me.