Stepping the mast is much easier in the water with a gin pole, if you have access to one, as follows:

(1) Position the mast with the top resting on the stern pulpit and the butt end on the bow pulpit, and attach your masthead fly.

(2) Attach backstay and aft lowers.

(3) Close sliding hatch over companionway.

(4) Attach loop of a line around the mast under the aft lower shrouds, leaving a 6-foot or more tail so that you will be able to retrieve the line after the mast is up.

(5) Attach the jib and or spinnaker halyards to the stem or forestay.

(6) Attach the hook on the end of the gin pole cable to the loop of line around the mast.

(7) Make sure the boat is positioned so the mast step is a little behind the end of the gin pole.

(8) Make sure the back stay isn't tangled and that the aft lower tangs are straight.

(9) Have one person crank the mast upward slowly and with the other person positioned on the deck steadying the mast.

(10) When the mast is high enough the person on the deck moves it forward and pulls the butt end down into the mast step and inserts the pin.

(11) Then the person on the deck fastens the spinnaker halyard and/or the jib halyard to the stem or to the bow pulpit and tensions them. They and the aft lowers and backstay will secure the mast in the upright position and the forestay, uppers, intermediates and in-line lowers can be attached at your leisure.

I have stepped my mast on occasion with one other person, both with the boat in a slip and on a trailer. However, it's much better with three rather than two people. And I prefer to do it on the trailer than in the water because the the boat may rock a bit in the water and damage the mast step once the pin is in.

I store my boat indoors and when I unstep the mast, using the gin pole, I detach the turnbuckles on the uppers, intermediates and in-line lowers, but I leave the aft lowers and backstay attached. I detach the forestay turnbuckle by easing the backstay and pulling the mast forward with a jib or spinnaker halyard attached to the pulpit. That way I never change the length of the turnbuckle on the forestay and the length remains correct until the mast goes up again in the spring.

David, what is your home port? And what is the hull number of your new boat? If you are anywhere near Detroit, I suggest you plan on the Detroit NOOD next June.