The standard tang has three holes. The main shackle that carries the shrouds and forestay use the lower hole on the tang. These hang from a 5/16" shackle. The 1/4" shackle for the trapeze wires hangs from the top hole. The "hoop" or bell of the shackle passes through the larger/center hole.

Be sure that the jib halyard wire is routed cleanly. Shouldn't be another cause there.

After hoisting the main, I hook the halyard at the top... then bring the halyard out, aft and around the starboard shroud. I then loop the line under the downhaul cleat and only then do I tie it off on the starboard mast cleat. Pull enough tension to keep the kinks out. That will keep it well clear of the jib while tacking.