Simplest/safest plan to raise mast
The simplest and safest method I know of is to hire the Marina to raise the mast for you if you've never done it yourself. I did and fortunately, I was there to participate so as to see firsthand how it's done. Now, I raise and lower the mast myself with one or two friends. There are several methods available out there for single handed mast raising but I would be very, very careful in doing so mainly because you're alone and in the event of any serious mistake, the obvious outcome is damage to either your boat or yourself. If you do raise it yourself, I suggest a rope attached to the front mainstay which is then attached to the bow's eyelets with pulleys. Keep in mind that raising the mast by yourself while propped up at the rear is not necessarily an easy task since it is somewhat heavy. A 3:1 purchase, perhaps even a 2:1 purchase may work, but I still wouldn't do it alone...scares the hell outa me! Good luck and good hunting!