Hi - I've just practiced with raising the mast on my new-2-me and after learning through the first set of snags concluded my main issue is the furled headsail (CDI furler). At least on this boat, it and the sail add quite a bit of weight to the mast, and I found its position hard to control, kind of like a very large eel having convulsions while attached to the mast.
I wonder if any of the wise sailors here have tamed this thing, or otherwise made it behave nicely while the mast goes up.
I bungee the roller to the mast when raising it.. just don't put it too far up (say 6' from the base) so you can undo it when it gets up.
Also I put a short bungee on the bottom of the roller drum, and the other end on the line that goes from the mast raising pole to the cleat so the drum is above the deck, but can slide down, as the mast comes up.
it does add some weight.. but if lashed to the mast, it is a LOT better than letting it sway side to side!
I just throw it over my shoulder while I'm cranking up the mast, and control it by shrugging it around as I go. Fastest way I've found.
To put the forestay pin in, I push down on the roller from the deck while the admiral inserts the pin from the trailer. If I'm alone, I push down on the roller from the deck with one arm and insert the pin with the other, but it's a heck of a lot more difficult. I bought a forestay lever assembly, but after breaking a shackle on the gin pole because I replaced it with a keypin shackle and suffering a mast fall, I'm avoiding any modifications to the mast raising/forestay system, and suggest you do the same. Especially do not change the ringding out for a any other type of cotter pin. The forestay and mast raising system should just be left alone.
The best speed mod I've made for mast raising is replacing the 1/4" bolts that hold the spreaders on with wire lock hitch pins. Removing the spreaders makes moving the mast between the bow pulpit and the mast foot a piece of cake, and the hitch pins hold them in perfectly well. I leave the spreaders off and toss them into the cabin while trailering. I shackle all the stays to the halyard which is cleated off and then put the spreaders and lines in the cabin. This keeps the stays and lines well managed on deck while trailering. I guide the stays through the small gap in the hatch while closing, and toss the jib lines and furler lines below as well. That keeps everything from flopping around or coming loose on deck while on the freeway and it's very fast. When it's time to setup, I move the mast back to the mast foot before putting the spreaders back on. I will say that the mast bounces a bit more without the spreaders off while trailering, so use a good truckers hitch and one of the docklines to tie it down to the cockpit-forward stanchion plates if you use this method. Don't worry, you won't bend the mast this way, and if you're worried about it, just swap which side the mast is laying on each time you trailer.
I also use a wirelock hitch pin to hold the boom onto the gooseneck. I leave the gooseneck assembly on the mast, taking off just the boom when it's time to put away. To take the boom off, I put the sail cover on deck upside down below the boom, flake the mainsail over it, disconnect the vang and the mainsail at the deck using quick-pin D shackles (leaving them connected to the boom, remove the boomkicker from the mast, and toss it all onto the sail cover. I then wrap the sail cover over the boom and mainsail and button everything up with the fasteners at the top. I then open the deck hatch and drop the entire boom assembly onto the cabin sole, where it fits perfectly from the forward V-berth to the clew end which sits between the ladder and the galley. Setup is the reverse.
This method has gotten my rigging and de-rigging down to about 20 minutes total in and out of the water. I trailer about 30 minutes to the water.
Thanks, guys - insights much appreciated. The idea of quick release pins for the spars is neat, as is tying off the furler drum. I
Since the furler-forestay is fixed length how do you tension it - by the stays? There is an interesting video on YouTube showing an owner who had the head of the forestay & furler on what looked like a track of some kind:
I have the furler head on a harken track and car setup. You can go to my website to see the modification. (the web server is down now due to Hurricane Irene, should be back up soon)
I can tension the rig properly if I wanted to get more performance sailing, but I'm a casual sailor and religate performance to how fast I can get it in the water.
If I were to properly tension it, I would adjust the turnbuckle in the drum and buy a back stay adjuster to add and release tension.
A couple of years ago I felt my forestay/furler looked a little "saggy" so I tightened up the side-stays by "two holes" (about 1/4"...each hole was about 1/8"). And this definitely tightened up my forestay. I had a harder time pinning it so I know it is tighter. I have to "over tighten" my mast-raising system to get the pin in and then when I take of the mast-raising system and the mast pulls back my forestay is much tighter. I did use a Loos Gauge to measure the tension on my side stays but I don't remember what the numbers were. I am sure there is a post from back in 2007 time frame when there was a big discussion on using a Loos Gauge.
I have never adjusted the turnbuckle inside the furler drum.
I use the over-the-shoulder method as well. Seems to work ok. The I'm gonna try attaching it to the line forward the mast raising pole. I'm not fond of scratching the deck (again).
On a related topic, should the mast have any bend in it at all when at rest? I I loosened the lower shrouds one hole because there was a very pronounced forward bend mid way up.
and after learning through the first set of snags concluded my main issue is the furled headsail (CDI furler). At least on this boat, it and the sail add quite a bit of weight to the mast, and I found its position hard to control, kind of like a very large eel having convulsions while attached to the mast. 
to contend with
owner who had the head of the forestay & furler on what looked like a track of some kind:
