The better helmspeeps I've tripped over, in my long years before the mast, made a point of helming from leeward, precisely to watch the jib telltales, etc.
I'd challenge you on that as my experience, it was always the 2nd rate helms who sat to leeward. Why....
Sitting to leeward, the helm cannot see what is going on around the boat, can't see what gusts are coming in, can't see what's happening to the opposition, is sitting in the disturbed flow from the rig etc etc and also means that the helm's weight is in the wrong place.
In old (early 80's older) keelboats, the wheel was so small in diameter and the stern narrower that you couldn't see the luff of the genoa or see beyond the crew sitting on the rail so there was a certain rationale to sitting to leeward rather than directly behind a small wheel.
Going back to double wheels, I first remember seeing double wheels on the 12m's ('83 or earlier) and they were used specifically to give the helm a better view of both the boat/rig and of the area to windward. The helm always sitting to windward.