Update on my jib furling issues: Since the forestay is only installed as additional mast support for my trapeze kit, and I won't be hanging off the trap any point soon, I have removed the forestay temporarily. There is now nothing for the jib to get caught on when furling and all is well.
Q: "What happens when you DO want to reattach the forestay for the trap?"
A: If you take a look at the pic below, you'll see a disk that is supposed to help keep the forestay away. I now have a disk from the good folks at C&L which is almost double the size. I'll get this installed soon to see if it resolves the issue once and for all.