I have the extra tall mast stand on my trailer and put the winch near the top. It is high enough it will lift the mast while it is resting in teh rear mast cradle. I use the winch attached to the forestay to do the hard work. I have my crew crank it up while I stabalize it side to side from the tramp. I the hold it up when fully stepped and have the crew attach the forestay.
I'm sure I could modify my setup to accommodate solo stepping but I have not taken the time to do so. It would involve adding the second set of trap wires so I could use one set to stabalize when teh mast is low and one more wire to do the lifting.
I have stepped the mast without the winch. It can be done, but is not worth the effort. It is hard to lower it after a long day on the water.
You will be fine. Good luck!
In the market
Previous boats owned
'74 Pearson 30
'82 H18 Magnum
St. Louis, MO