More asymetric questions

[Brian Duff]

Yeah, I would say if you want to use two pole lifts , to wing out two sails downwind, you would need two pole lifts. A pad eye with two 1/4" fastners should be enough for a dedicated lift on that westsail, and you can use a horn cleat on the spar if you want, cam cleats or a jammer would be easier to use, but a cleat works too, and are pretty much failsafe. I normally install a through deck block in the front of a the spar, pretty far up, and then cut an exit down near where you want to cleat the lift, so that the line runs inside the spar. less windage and noise, sometimes less chafe problems on the spar.. Cleaner looking too.
What is 'strange' about the mainsail arrangement.you should consider hanging a snatch block on the end of your boom for the jib sheet, then you can run the boom out with a preventer, the sheet and your mainboom toppin lift to stabilize it, and use the main boom as one pole and your pole as the other. save money, and weight, and complication, and clutter.
Did you get a decent arrangement for the halyard sorted out ? as no one directly answered you , no you cannot use a spare jib hal as your spin, you need a halyard block mounted outside and above the headstay.
Good luck.
Brian