Tim-
I'm a newbie to the 36 Mk II, and inquired about the same issue on my 2005 C 36. Based on reader feedback- I played with the topping lift/boom elevation, checked to make sure the mainsail was tightly wrapped to begin with, checked for reefing line interference with the mast etc and found that only the tight mainsail wrapping helped. Some readers indicated that lubricating the boom track and car bearings should not be attempted but others voted for it. I tried McLube Sailcoat drylube from West Marine. (Or some product sounding like that). It worked very well. Not a perfect solution, but 90% improvement which I'll take over sending crew on deck to free the car in rough water. I've only sailed twice since its application so I can't speak to it's durability.

Paul Keyser
First Light
2005 C 36 MK II # 2257

Tim - I think the problem may be that the furling line is too thick for the amount of space that is available on the drum. So when you unroll some of it - then it does not rub against any other part and it unrolls easily. You may try adjusting the block that guides the line into the drum so that it does not over wrap itself when furling. I normally wrap the jib while on down wind point of sail. If you have a jib that is 150% or more it requires a longer line and this may be the cause of the added friction. Use 1/4" or 5/16 line if your line is larger.
Let us know what you find.

Tim... check too to see if the outhaul line is rubbing against the cage around the lower unit. It is fastened with a hex bolt under the cage and if it gets a little loose, it moves the cage over to where the line rubs against it causing additional friction. It may get easier to haul out after the initial few raps come off because you are getting wind assistance in the sail pulling it out.

The other part of the problem could be the bearings in the lower unit. If you have a Schafer furling system, on older models (and I don't see where you mentioned the age of your boat) the didn't allow for flushing the bearings with fresh water. Myself and a few others had this problem and had to replace the lower unit. Schaefer knows they had this problem because the replacement unit has a flush hole with a big arrow pointing to it with a label "Flush". If you get on your knees and look into he furler unit when the sail is furled, you ought to be able to see the flush hole unless you have a lot of extra line on the furler... then go back to a previous comment about line and line size.