I feel your concern. A few months ago, while moving marinas, I was forced to drop sail, and motor for almost 20 hours, just because the (very odd cold front had changed the) wind direction so it was Dead astern. I was not prepared for this at the time, and have made sure I will not be unprepared again.
I have since played around with a few configurations. I have a 32' columbia, My whisker pole is (non-adjustable, I prfer something can never "slip") and just short of 10' in length. (I run a 140 genoa) It has a quick release piston type on each end... and is symetical, so completely reversable. It makes no difference which end is on the mast and which is out.
My boat had the option of being "cutter" rigged, but it is not, however, I do have the halyard about 80% up the mast that is rigged. I use this as a topping lift for the whisker pole.
And, there is steel rigging
running the length of the whisker pole (permenantly attached) that has a RING positioned dead center, (again, symetrical rigging
I place a block on my toe plate then from a mast cleat
, through this block, up to the aforementioned RING. This prevents lifting.
Although I realize the advantages of seperate guy lines
(safety), I have found that a sizeable stopper knot (figure 8 or modified surgeon) in the gib sheet, o either side of the whisker pole close to the clew, works better for me. This prevents the jib
-sheet's bowline from getting tangled/caught up in the pole..... However it is important to understand, I only do this because I can take 3 steps..pull the quick release piston.... and all is dropped and de-powered....I would not do it other wise.
The only other thing is, if you want optimum speed, (and safety) you should rig
up a (gybe) preventer on your boom. It is CRITICAL (at least in my mind) that you do this with the ability to controllably release the preventer line
while taking up the main sheet. I use my spinnaker
wench for the preventer (or the opposite jib
wench).... ensuring I can release it all the way to broad reach on th opposite side if need be...(not that i can foresee me needing to do that).
I have run this set up half a dozen times now, and have become quite comfortable with it...... but, I still consider it an "open water" config, as (especially single-handed) visibility is compromised at best, and maneuverability is no where near where i like it.
I recently took some video of this "set-up" for a friend. It is at the Marina tied up, and of course no cloth flying, but u can see all the rigging and get the idea.
if you would like I could prob, flip to U-tube and show via this site. lemme know if u are interested.