Lowering the Mast
I have to lower my mast for winter storage and this past winter was my third time doing so.  There are three of us who take our boats out at the same time and we work together.  Also, we use a gin pole.  Actually, two people and a gin pole make the job really simple (takes us about 20 minutes to actually lower the mast and secure it in place.  After positioning the boat under the crane portion of the pole, the procedure we use is to first secure the crane hook to a bridle (made out of spare dock line with the running end secured to a cleat on the lower end of the mast).  When tension is taken on the gin pole hook, the bridle slides up the mast to just under the shroud connectors.  This height may be controlled to some extent the running end of the bridle line.  Actually, though, even when the bridle is all the way up under the shroud connections, the mast is still top heavy and needs to be counterbalanced.  Next we loosen all shrouds and stays disconnecting both fore and aft stays (I have a roller furler so some care must be taken not to damage it or its components).  Once the shrouds are loose, it is optional whether to remove them from the chain plates or not.  I do.  Then, one man controls the lower end of the mast while the other lowers the hook thus lowering the mast into its stowed position.  Care must be taken to secure the mast in the stowed position as well as the loose shrouds and stays.  Raising is just the oposite and takes about 30 minutes (not including shroud and stay tunning).