Re: Jib furler is hard to furl since putting up new sail...ideas?
Ditto on halyard wrap.. you'll either need a halyard restrainer, or add a pennant to the sail so that the swivel is back to full hoist.
If that's not it, I'd think there will be some considerable difference in how a beat up, worn out lightweight sail rolls up compared to a new, stiff, UV covered one...
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)