About setting that poled out jib ... Someone had mentioned gybing the main, setting up the pole behind the main then gybing again. Some say it's best to attach the pole to the jib clew ... I prefer to the sheet as it seems to allow for more flexibility ...
A bit of research shows that an alternative is using a setup similar to what you'd do for a symmetric spinnaker but with two afterguy sheets: one to bring the pole back and one to pull the jib over. Three lines are used to keep the pole in place (topping lift, foreguy and afterguy) and one sheet is run through the pole jaws to the jib clew. That's a lot of lines for a single guy
https://www.youtube.com/watch?v=II589dqAzLo
Now ... sail changes take time. Let's think through this. It's day time and I've got the spinnaker up (do I?), cool. Night's coming with its suit of squalls. I want to "simplify' to a poled out jib. So I bring out the #2, lay it on the deck, rig the jib sheets and the jib's afterguy sheet, knowing that I'll have to put it into the pole jaws. Ok, so down goes the spinnaker, flawlessly of course. I now run the jib's afterguy sheet in the pole jaws. I rig a second afterguy sheet and position the pole out there, maybe at 45 degree. Next I hoist the jib to leeward and then pull it to windward with the jib's afterguy sheet. Voila ...
Wait ... I want a longer pole for this ... Darn I need to switch poles!
Let's resume this exercise. Jib on deck, jib sheets on, long whisker pole on deck but not attached to the mast, jib afterguy through the whisker pole jaws, whisker pole afterguy rigged (where it goes I have no idea as I'm running out of choices there). Down goes the spinnaker, back on deck to drop the spinnaker pole, move the topping lift and foreguy to the whisker pole, secure the whisker pole to the mast, move the pole out to 45 degree. Ok, hoist the jib to leeward and pull it through to windward. And voila ... Yes?
I'm probably down to the main for 30 minutes there ... Maybe once the spinnaker is down, I hoist the jib and head up a little to keep some amount of speed.
Just thinking like a racer is tiring ... Cruising anyone?