I've sailed on and off over the years, but this is my first boat, so I'm new to the Helm!
We don't have a furling jib or main, and sail with the smallest jib (#3 I think) in wind >20 knots.
The lufting main was a result of us trying to avoid the heeling, boom was out too far.
We only reefed the main once, but had a kink in the line (i.e. prevented the clue from being pulled all the way down to the boom) and it resulted in a cup full of air in the bottom of the sail! Maybe THAT was my problem!
I like your idea of bringing someone out and helping us through this!