Re: Jib furler is hard to furl since putting up new sail...ideas?
You got some good replies. I'll take it a step further;
1. Release the tack and raise the sail to the top. If it furls easy you can choose to add a short penant to the head or foot of the sail. Many people choose to have one made of wire, but, modern low stretch braided rope will work well. If the it's only a few inches, make it yourself out of rope and attach it to the foot where you can see it. Might even give you a little bit extra visibility under the jib.
2. Play with the halyard tension. Too loose is bad and may cause wrap as others have suggested, but depending on the system, sometimes too tight will bind things up as well.
3. When you first try to furl, do it from the bow pulling directly on the line, avoiding any other hardware. This will help figure out if it's something in the deck hardware as someone else mentioned.
4. Try it on a windless day with a cold beer for best results.