The Text Version...
No E-23 experience, but have owned two prior boats with hinged masts. Also helped a friend with his ODay 23 mast once.
Our first boat was a trailerable Ranger 20. That spar was walked up, from the bow, and we did this many times. Little tricky at the 45 degree angle position, and not a task I liked doing afloat.
The ODay 23 spar lowered forward, with the boom as a gin pole, and guys on the end of the boom, and on the spar, to keep both in allignment while hoisting or lowering. I applied that information, years later, when it came time to lower the mast on .......
Our Niagara 26 had a 34 foot spar. It had a hinge pin in the step, but was quite a bit of weight for us to handle. We put it down and up twice in the decade we owned the boat. On that rig we used the spinnaker pole as the gin pole, and lowered it aft to a homemade crutch mounted on the stern pulpit.
Again, the main winch work was with a line from a snatch block at the bow fitting back to a primary winch. The spinn halyard was secured to the end of the pole from the top, and the end of the hoisting line to the same pole end for the down force. On the mast I would lower the bull ring to the lowest position.
There were two side lines (guy lines), hauled up as a pair with jib halyard and then taken to snatch blocks on each rail across from the mast step. Problem is that the pivot point for the mast foot is higher than the rail... so you have to adjust those lines every couple inches as you lower or raise the spar.
Finally, as you noticed already, you do have to guy the end of the gin pole (whether it's the boom or a spinnaker pole) to keep it in plane with the mast.
We also led these guy lines to blocks on the rail and back to the cockpit. Luckily our N-26 had secondary winches...
Anyhoooo, we took it slow an easy, with two of us cranking and tending lines. Hardest part, really, was lifting the whole weight of the rigged spar while standing on the lazerette, with the othe guy holding the foot of the mast down (!) when it came out of the step, and then slowly walking the whole shebang forward to get the spar finally resting on a wood support at the bow and the stern.
No pictures, wish there were some to share...
Loren