Raising the Mast
I raised the mast on my first boat (Laguna 24), not much more than a C22 by using a crutch at the transom to slightly raise the mast. I would attach the shrouds, attach the jib halyard to the bow tack plate, raise the mast (it wasn't that heavy) take up the slack on the jib halyard, cleat it off on the mast cleat, then go forward to attach the forestay. That was 25 years ago, but I am sure I could still do this today (I'm 64).