Tarheel, I am fairly new to this too ( 1 year ), and I came up with a winch set up which allows me to raise the mast without using much force at all. I will take pictures next time and post them. But for now, let me give you a bit of advise;
*Before you raise or lower the mast, place a good safety rope around the lower first foot of the mast, close to the pivot point. This will prevent the mast from shooting forward in case the lower pivot pin comes loose or breaks when you are raising the mast. If you do not have a rope to hold the mast next to the pivot, it will suddenly unbalance and it will just end up on the ground and can even kill somebody.
*Replace ALL the pins with new ones, if a pin gives up, same, mast down. It happened to me while sailing.
*Always keep eye contact with the Boom bar when the main Sail is up, it will whack you and you`ll learn why they call it the Boom !!!
*Learn to do ererything solo, from Home to Sail and back to Home, you will enjoy your Hobie even if your girlfriend does not show up ( Well, she will always show up if she knows you can solo )
* Always watch where is the wind going, towards the Sea, or towards the Land, if you have winds that will push you away from safe land, carry a portable-waterproof VHF handheld, it can save your life.
* Carry a portable GPS and always look at your speed while sailing, this will help you learn how to adjust the Sails for better speed, as you can see the actual effect on small changes.
* Make sure your Hobie is rigged in such a way that if you fall from her, it will self point upwind ( in irons ) and just stops sailing by itself.
Carry water and food bars with you for just in case you have to sit and wait.
Good luck !!!!!
Every second that passes cannot be recovered, so make good use of every one of them that you have left.