single handed raising.
To do it single handed you need to rig a block at the pointy end, then run a line from the mast head, through the block, then back to you. This would most likely be a halyard, properly attached at the other end, of course. If none are long enough, tag another line on the end. Run that line, coming from the masthead, through the block, and back to where you are when you start to raise the mast. As soon as you lift it off the deck, start pulling on the line. Before raising it far off the deck you can use it to raise some or all of the weight of the mast. If you get into trouble, you can cleat it off or hold it by the line.When the mast gets all the way forward, just tie off the line and you can take your time doing whatever else you need to do.To make it easier to raise, instead of putting the block on the bow of the boat, build a mast on your trailer that extends far higher than the bow. I use a 4' piece of 2" square tubing mounted on the front of the trailer, with a 4' piece of 1 1/2" tubing inside. Before raising the mast I put my block with the line rigged through it on the top of the 1 1/2" piece, then raise it the 4', stick a pin through holes in each, giving me a pulling point about 8' higher than the trailer.To make it even easier, instead of just tagging a line to your halyard, use a block and tackle rig, compounded as many times as you like, and you can get enough effort that you can raise it by yourself right off the deck just by pulling on the line.When it's up, cleat it off and take your time. I use this system all the time.