This post won’t help rgranger much, but it’s interesting. If you have the engineering know how and fabrication skills, you can build a mast raising system that works in moderate winds and sea states. (Or you can pay a boat designer/ architect to design it and then contract with somebody to fabricate and install it.).
The Dutch have been dropping masts so they can squeeze under bridges for centuries. Google Beoier sailing barge and Botterjacht. They have been used for centuries to transport cargo in the Netherlands. They generally have masts in the around 50:feet tall. The important features In their systems are a tabernacle hinge positioned well above the gooseneck, an A-frame for a lifting point, and an (optional) counter weight on the foot of the mast.
Their mast feet go below the deck ( through a trap door in the deck in front of the mast ) and are counter weighted on the bottom. They are engineered to withstand side wind and moderate wave conditions. It’s clever because no only does the counterweigh take the work out of lift the mast, it also does double duty as ballast located at the bottom of the hull.
For well thought out systems in smaller boats, Take a look at the Marshall sanderlings, and the Compac Suncat for examples of tabernacles masts with the pivot point above the gooseneck. THey don’t require removing the boom or mainsail To drop the mast. Since these are comparatively short masts, They can be easily dropped with no need for a counter weight on the foot of the mast.