It can also depend on how your boat behaves. My boat is quite happy sailing to windward on just the jib so I can put the tiller pilot on and drop or reef the main in the shadow of the jib. My previous boat was very good at heaving to so that was useful to get things sorted.

I followed an idea here which is to put a cable tie round the fixed end the reefing hook and across the hook so that it acts as a gate. When I go forward and hook the cringle on then it doesn't fall off again before I get back to the cockpit.

Having lazyjacks and a stackpack makes all this much easier single-handed.