I furl the jib when going downwind rather into the wind. I find that going into the wind causes the jib sheets to flog and sometimes break the glass windows on the dodger.
Let out about 2 feet of the jib sheet then roll in then ease the sheet a little at a time, and continue rolling in.
 

Joe....is the furling a problem when not under any stress? A number of people have had problems with Schaefer furling gear because the older models have no flush hole for the bearings and eventually the bearings seize up. Schaefer has a replacement with a flush hole so they know the original was not a good design. Mine was tough to furl and then, after one winter, the gear would not turn at all.

While I have used a winch to crank on the furling line, it's not a normal practice for me.

I suspect too much tension on the sheet when furling.  Try furling at the dock under calm conditions, again with just slight tension on the sheets, and see what happens.  If it rolls up nicely, then it's a matter of wind load on the sail is too high.  We tend to head up and then let some sheet out while at the same time hauling in on the furling line, trying to strike a balance between furling line effort and sheet tension.  While it can be a one person job, trying for that balance is sometimes tough, so I usually ask my mate to slack the sheet while I haul in.

I know this post is a little late but I noticed this issue on my first Catalina ( a 25 with a 150 gen).  When in higher winds I could not furl upwind. A dock mate suggested that my head stay might be a little loose and the droop was causing an issue.  Next chance I had - we tightened the back stay and had no problem bringing the head sail in. Just left it that way unless the wind was really light. Our 36 has a 110 gen and we never have and issue furling it, but I keep the back stay pretty snug by default.

I also had an issue with our Hood Seafurl jib furler turning hard two years ago - drum and halyard bearings were fine. Discovered the top clamp screws had come loose and the clamp was rubbing on the extrusion as it turned. Lifted the clamp and tightened the screws and the problem was solved.