I have a 2003 Hunter 44 Deck Salon. I am getting the furling wheel on the mast replaced this week as the new lines I just had replaced are slipping round the wheel when furling in. I don't know if this will help it or not.
I had the same problem on my 2006 41. It seemed particular to go in and out. You had to have the boom set just right and tensions on outhaul and furling lines just right. I brought it to my sail maker. here is a picture and his take on it.
Sail Shape —
The cloth this sail was made from is soft and "mushy" and by nature not great for shape retention. This, combined with a simple cross-cut construction exacerbates the situation. Suspended, with no pressure on the sail other than it's own weight, the sail is about three times deeper than it should be. This excess depth makes for a very draggy shape. It causes excess heeling, forcing you to reef early. And it's slow. Just sayin'.
Functionality —
1. The excess depth impedes the sail from rolling in and out cleanly. The crescent creases you see in the photo below are caused by the "fat" folding over on itself as you roll the sail into the mast. This folding over makes fat irregular wraps causing the sail to choke in the mast opening and can lead to major problems when you need to furl.
2. Note the rippled foot tape. This happens because the whole foot is on the bias and therefore completely unable to resist stretch when you pull the sail in and out. If the sail is reluctant to go in and out, the load and stretch on the foot is increased.
3. The clew block is really small. If the outhaul rope is any fatter than 3/8" that will be an additional source of resistance when you want the sail to go in or out. i don't know for sure but I'd be surprised of the clew outhaul was that size. You could downsize the outhaul by up-spec'ing it.
4. The sail shows a mildly sunburned edge where the cloth is exposed in the mast slot.
You mentioned high effort furling the sail and the lack of a proper slide for the clew outhaul. Certainly that is the biggest effort related issue but it has no bearing on whether the sail folds over on itself and whether it might choke in the slot.
This was his recommendation:
It just so happens we have a solution to the issues laid out above —
1. We prefer to make our into-mast mainsails with a tri-radial cut.This prevents stretch through the belly of the sail so it will not "grow" at all for it's entire life. A Radial tack and clew puts the foot cloth on the thread line not on a bias. Thus the structure of the cloth is properly used to resist the pressures on it. T-R sails can use lighter fabric in the "front" so they roll up smaller. Of course this makes them lighter as well.
2. We suggest laminates rather than woven fabric for it's greater stability and reduced mass (which translates into volume)
3. Being flatter and because they don't "grow", they roll up neater. Neater on Day One and all the way through the sail's life.
4. We recommend an upgraded clew block with more room in the swallows to a suitable outhaul line.
5. We put sun protection on the leech edge of the sail
Of course, these solutions are not the low cost way to do it. We can also make a more conventional cross cut sail out of firm cloth that isn't so mushy and stretchy. We can skip the edge cover and reuse the clew block. We can "trip" the first panel so the foot edge is on thread line. These build options will save quite a bit and the result will still be much better than what we saw today.
I have never been happier with a set of sails. The furling works perfect ever time and the sail unfurls like butter. I do one wrap around my port cabin top and tail the outhaul onto the starboard cabin top winch. I pull the line from the center as it is streached over the companion way. I pull it one handed and I'm done in 30 seconds. The sail shape is always excellent and they look good to boot. Way over kill for a cruiser but I keep up with a buddies 47.7 Bene. I don't tell him his main is streched and it's an wind anchor I like walking him till he puts up that big spinnaker
I used to reef around 14 knots and could never get the sail flat, now I reef at 17 and can get the foot dead parallel with the boom. I have a lot less heel at all wind speeds when close hauled and this makes it more enjoyable for guests.
My sail maker is in Stamford Connecticut and makes racing sails. But I always suggest finding a local sail maker, not one that just takes dimensions and copies what is essentially an old stretched sail. I'm sure you will find a lot of opinions about sails but I find this works well.