iron it

put a loop of rope at top of sail (prydes come with this already), so you can stick screw driver in ground and pull mast out without scrunching up the sail. There's half of the battle.

roll the sail, don't fold it.

Further to Mark's comment about tying down the sail head and pulling the mast out, it helps a lot if the mast is lubricated. Spray Sailcoat on the mast a few times and it coats the inside of the luff sleeve. You'll have your sails going "Oooh ah, I'll have what she's having". (All sails are female if you hadn't noticed)

geez my wife has been rigged a lot

here's a good protector in advance..go to nearest sticker shop and have laser printed your favorite logo onto 3m monofilm sticker paper and apply on the most likely creased spot on the main panels. looks good and will prevent wear and tear..

One of my masts developed thousands of tiny carbon splinters all over the surface - apparently this is due to over use in salt water, and exposure to UV breaking down the outer layers of epoxy..

Advise ranged from 'throw it out and buy a skinny' right through to 'give it to me - I have tough hands'.

In the end, I gave it a tickle with some 600 grit paper, and sprayed it with a couple of coats of clear spraycan laquer to stick the prickles down, and it's been great ever since.

As an added (and unexpected) bonus, this means that the mast is now really slippery when wet. It's easy enough to rig up without creasing the sail, but it's un-rigging that used to cause me problems. Now that the mast is slippery I give it a bit of a twist, and it just slides right out without any fuss at all.

Failing that, DryGlide.. made by CRC I think.. (haven't had any experience with sailcoat, but I imagine it's similar) It's a teflon spray which dries (so you don't get silicone everywhere) Typically used to help yacht sails go up the track in a mast, but it should work just as well the other way around. I dryglide the joints on my masts.. haven't had one get stuck since I started spraying them.

Any good boat chandlers should have it, and maybe some hardware places?

It's a lot more expensive than a can of clear spraypaint though!

The best stuff is "Mclube Sailcoat" available from any decent ship chandlery. Whitworths has it for around $18 a can.
Spray top and bottom halves of mast obvioulsy giving the area around your boom height or cutout a wide berth. You dont really need to go right to bottom mast either to save for further applications.
After several applications the mast will be heaps easier to slide up sleeve and it coats the inside of sleeve for much easier rigging.
Also seems to help sticky cams to rotate as well.

www.mclube.com/sailing-boating/

Interestingly, it says "will not attract dirt or contaminants and will not transfer to other surfaces, or you."

Not sure how true that is though if people are saying that it will coat the inside of a mast sleeve?

My favorite old sail (North Convertigo) has panels of fabric (Dacron?) about 8 inches wide all the way down the length of the sail, between the luff tube and the monofilm/x-ply panels. When rigging and de-rigging, the fabric gets all crumpled up but the monofilm just gets gentle waves in it. It's a really old sail but there's no crumple marks in the monofilm yet. A really clever design, methinks. I wish new sails (Ezzy especially) would come with this feature.