The only time you'd want to fly two at once is well off the wind
. If you're going to be hours and hours that way, you can set the luff grooved one to windward with the pole, and your light air jib
to leeward, flying (not hanked on or in a groove).
When you want to take the second sail down, you gybe so that it lies along the inside of the furler sail, and, on the foredeck, with the halyard
in one hand to ease it, ease it down while using your other hand to flake the head
of it. When it's down, secure the halyard
, untie the sheet (and secure it), finish flaking the sail, roll it forward, and tie with the gaskets (sail ties) in your pocket and bag it. Not hard to do when you are not rushed, and have thought it through.
With the main a bit over trimmed, for roll dampening, it can be a pleasant way to travel.