I guess the key to your question is what local rules you are using. Most PHRF fleets specify several divisions under the basic PHRF rules. And by design, the local rules are specifically composed to fit what the racers in that area want. Thus the extreme diversity in local rules between PHRF fleets over the US. And they are ALL RIGHT for their own areas. I am fleet captain this year for our club and we have a
spinnaker, nonspinnaker and a cruising fleet. While we permit mylar or kevlar sails (not simly white sails only) in our cruising fleet, we do not make any distinction between fleets as to the whiskerpole use as to which side. We go with present rule which permits use on either side of the boom but must be connected to the mast. Clearly shown in the existing RRS. But this may be contrary to your local PHRF rules.
Having this capability really increases your management of your sails. Being able to trim the pole when on the same side as the boom (pole to leeward) is a tremendous feature. But to do so means you must be able to have a variable length pole and be able to immediately and constantly change this length to get the best our of your sail. So by adjusting the pole length and adjusting your jibsheets, you can make a wonderfull air foil.
We always sail shorthanded and solve this pole adjustment by installing additional T track on the front of the mast. We use a whiskerpole extended to the maximum allowed. By using a halyard we hoist the pole which one end has been connect to the
spinnaker mast car. We have a
chock installed at the bottom of the mast to hold the "free end". To use the pole to leeward or windwand, we simply un-chock the free end and snap it into the genoa clew. Then by lowering or hoisting the mast end of the pole, we can do some real fine tuning of the genoa trim. So the pole stays the same length regardless of the headsail you use. You do have to deal with the extra weight up high but we think it is worth the weight. Jibing is really simplified of course.
If you are using PHRF go to the committee and request a change. Seems like this would be easy to do and I can''t see why they would limit you.
Good luck.