We have an O'Day23 which has a deck-stepped (hinged) mast. Any special tricks and / or additional equipment to make the process easier (safer) for my wife and me?
I think that two of the most important things to remember is the wind direction and making sure the boat is level. If you're stepping the mast from aft, you'll want the wind coming directly from aft. You'll need your stays connected with the exception of the fore stay. The fore stay can be bungeed to the mast so it does not flop around. I'm assuming that you're planning on raising the mast from aft. You'll need some kind of a mast crutch in the stern to hold the mast while you pin the tabernacle. If you have a stern rail, you could probably make something out of wood. Install a small roller in the crutch and you can roll the mast back into position. My friend Wayne made a detachable mast crutch with a roller in it that fits on his stern rail. I have something similar on my boat that you can check out in my Owner's Picture Album on this site.
When I was younger I used to get my mast ready at a height that I could reach while straddling the cockpit seats. Then I would walk forward and pin the tabernacle. I would stand on top of the closed companionway hatch and reach down and grab the mast and raise it by hand. Then I'd put my shoulder into it and push it up.
I installed a single sheave on the bow stem chain plate with a 60'X3/8" nylon line which I had attached to the Jib halyard shackle. I raised the Jib halyard all the way up and cleated it off at the bottom of the mast. I used this line to keep the mast in place after I got it up, by pulling it tight and taking it around the mast
above the goose neck fitting and tie it off at the bow horn cleat. Then I could let go of everything and connect the fore stay and insert the other tabernacle pin.
The above procedure works great if you're young and strong and your boat doesn't have a roller furler. A roller furler can really throw the mast off balance and cause it to go over sideways if it's not guided properly. The same goes for the wind if it's blowing hard on the side of the mast or if the boat is leaning on one side. The stays will only support the mast when the mast is up and this is something that you need to remember because if the boat is leaning to one side, the mast will lean to that side and will go over that side and break off the tabernacle.
The best way I've found to raise a mast is with a Gin Pole which can be made of wood with some metal hardware. You could use a small boat winch mounted on the Gin Pole to pull the mast up, or you could use a good size boom vang or block & tackle set up like I do. The line on a boom vang probably won't be long enough so you would need to put a longer line on it as I have done.
Since I reached "Geezerdom", I've found that the Gin Pole is the way to go especially with a roller furler connected to the mast. Because I have a heavy furler and I raise/lower my mast by myself, I've gone the whole route and installed temporary stays (baby stays), and pivot bridles on my boat. This gear provides the mast lateral stability needed when the mast is either going up or coming down.
When you're raising your mast you want to keep an eye on the stays and turnbuckle toggles. Make sure nothing snags the stays and the stays don't get twisted. Take it slow and easy. That's it. I think that I covered everything except that you need to watch out for overhead wires and tree branches at the ramp when you get ready to launch your boat.
Joe