Cue the chorus of voices who, ignoring the request of the OP that he is not interested in the pros and cons of in-mast furling, will snidely insist that he got what he deserves for having in-mast furling in the first place, and go into a lengthy diatribe about why.
As Bash said: the system is not inherently prone to jamming. I have had exactly one jam in mine in going on a hundred days at sea, and that was due purely to my own inexperience.
What I found is that you need to be very careful about the angle of the boom -- on my boat, at least, the boom needs to be absolutely horizontal. The point is -- as Bash said -- to have equal tension in leech and foot so that the sail is smooth and flat as it's being hauled in. You can change the balance between the tension in leech and foot by changing angle of the boom with kicker
and/or topping lift
Second: be careful to keep some tension on the outhaul
as you bring in the sail.
Both of these things are obvious and logical if you think about it -- the tension from the clew needs to be correctly aligned in order to keep the sail smooth as it is rolled in.
After my first (and admittedly traumatic) jamming experience, I have had no further problems.
I don't think there is anything wrong with bringing the head
to the wind
when you furl. I think I get a somewhat better furl this way, because the back tension comes all from the outhaul
and is thus more controllable. But I can furl off the wind, too -- the system is not too sensitive to this, at least on my boat. Being able to furl or unfurl (reef or unreef) off the wind is one of the great advantages of the system.
If your sail is all blown out, then that could be your problem rather than improper furling technique. But if your sail is all blown out you have other problems as well. Replace it in that case.