I agree with Merrill; replace the furling line
You are not doing anything wrong. I had exactly the same problem on Dragonfly a 2003 B331...worked great at first, harder each year. Had to use Larry's approach of going to the cabin top to pull the sail out. Almost impossible last fall and had to use a winch past half way out.I replaced the furling inhaul line this spring with 50 feet of new 5/16 line. Works great! It was so free and easy that I almost hurt myself the first time as I pulled too hard!I had problems a few years ago with a drum bearing freezing and removed the drum. US Spar replaced it at no charge. That was a real job! Not nearly as easy as outlined in the manual. This spring, I replaced the line without removing the drum. The sail was off for the winter. Of course the line was rolled almost to the top of the drum. I tied a 1/8 inch nylon line to the sail shackle and pulled the inhaul line. This wrapped the 1/8 line around the furling foil.Next, I loosened the top two bolts and removed the bottom two completely. I was able to pull the bottom out far enough to pull the line out the bottom of the drum with a needle nose pliers. I cut off the end knot, removed the old line, inserted the new, tied a figure 8 stopper knot in the end, pulled the line to seat the knot back in the drum, replaced the drum, replaced and tightened the bolts, pulled on the 1/8 inch line wrapping the new line back into the drum. The entire process took less than 10 minutes.A word of caution. On Dragonfly, the bolts that hold the drum are hex head bolts that go through the mast and screw into a little rectangular steel block glued to the inside of the mast. When I removed the drum the first time a few years ago, the steel block came loose and fell to the top of the drum. I had to use a wire hook and long thin screw driver to capture the block through the inspection panel and hold it in place while I started the bolts. It was a real pain!! That's why I only loosen the top bolts.Good luck.Mark