Raising the Mast

My wife and I have worked out a great little system that currently works for us.  

She stays on the ground (she get's really nervous) and holds the forestay and forestay turnbuckle.  I attach the jib halyard to the bow plate in the aft-most hole as the middle I use for the forestay and forward most hole I use for the cruising chute's tack line.  With this attached and the mast sitting in the bow stand on the transom I give the jib halyard a single wrap on the mast winch, then standing in-front of the mast facing aft, I get a good grip with both hands and lift 'er up.  Once she's vertical, I move around behind it holding up with my chest and shoulder and take up the slack on the halyard (temp-forestay).  My wife pops up on the tongue of the trailer and sets the clevis pin on the forestay turnbuckle in the second hole.  I usually have to really lean into the mast to make it work.  This means less tuning of the rigging later, so I like that.

I find the faster I get it vertical the better, momentum and the shrouds become my friends keeping it straight and plumb. Although from time to time a shroud with get hung on the roller furling cleat on the starboard side... what a pain!

I know eventually, as I get older I'll probably have to come up with something better and less physical, but right now I don't find the mast that heavy.  I'm 42 and weigh 220lbs. so maybe I have a couple of things on my side, I can still do it and outweigh the mast by a few pounds.

My Method

I can lift the mast from on top of the cabin, but if anything goes awry (like a shroud hung on the roller furler cleat, or the backstay being under the tie down strap across the stern that I forgot to remove - crap!) then I could not gracefully let the mast back down onto the prop.  So having someone snubbing the fore halyard is my backup.  And since it's there, it's a lot easier to start the lift from the cockpit and then move to the cabin top while the helper holds the mast.
Your fore halyard is longer than mine.  Mine won't reach the bow plate, so I use the dock line to the fore cleats as an extension. 

When I'm lowering the mast is when the second hand snubbing the fore halyard really helps.  No way I could lower it from the cabin top and gracefully land it on the prop.