O'day recommended system
Shawn, My O23 (1982) came with a system which I believe was factory recommended. If yours is set up like mine it has two pins holding the base of the mast in the tabernacle.To raise the mast lay it on the deck with the top of the mast forward, over the bow, and the forward pin inserted. The outer shrouds and the forestay should be loosely attached. The boom is then set in place with the following lines attached - (1)The topping lift is tied on. (2)Just above the outer shroud turnbuckles is a triangular plate. Run a line from each plate to the aft end of the boom. I have lines which are pre-measured to the correct length to hold the boom square to the mast. (3)The mainsheet is run from the aft end of the boom to its fitting on the transom.When these lines attached the gooseneck can be slid into place and the lines tightened so that the boom is vertical.With a little help from someone on the bow lifting the mast you simply pull on the mainsheet. The boom works as a ginpole and the mast goes up slick as you like. Once up you slip the other pin into the base of the mast, attach the backstay and inner shrouds and tighten everything up.With this system you can raise and lower the mast solo. There is very little force on the mainsheet.If this description confuses you (it makes sense in my head but may not translate as well as I think) let me know and I'll draw a picture or invite you over to Brookville Lake to help me lower the mast for winter (is that a 4-letter word?).Good luck.