Re: Asymmetric and pulpit
We fly the tack pennant under our second anchor roller, ahead of the furler but inside the pulpit. It generally flies within a foot of the top rail height and doesn't seem to put any considerable strain on the pulpit. Our pulpit extends similarly to what you describe. I did try it outside the rail but it spent more time rubbing along the pulpit that way. YMMV, of course.
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)