I just got a Prindle 18 and I hear ya. It seems to take my whole family to put the mast up. Or at least 3 of us but we are getting better at it. First I bought small winch an mounted it on the raised mast support on my trailor. At the moment my wife runs the while I walk the mast up from behind the boat my sons jumps on the tramp and continues walking it up not so much lifting as offering some side to side support which seems to be our biggest problem.

Now I don't know much about the 16 or even my 18 for that matter but I was shown that if you can provide support lines from the front cross bar even with your mast you with have good side to side support all the way up. If you have trap line (I don't at the moment) you might can pull the shock cord around the front crossbeam on each side providing constant even support all the way up, You cannot allow for the side stays to help you as they do not offer any side to side support until the mast is most of the way up.

I think I could eliminate one person doing this if I can fashion about a 5-6 ft tall tripod mast stand to stand behind my boat and set the mast end in while I hook it to the step hinge. This i think would give enough height that the winch can immediately take the entire load to go up. Once I get a for sure method for supporting the side sway in place and the mast stand I think I could put up the 28ft mast alone. Still makes me nervous though. I just bent my Mast step hinge the other day because when lowering the hinge was somehow forced into the down position and the pin pushed down with it in such a way that it became stuck making impossible to remove the pin and thus disconnect the mast. So while teh mast is on it's stand (which is my sons shoulder for the time being) I to fiddle around and find a wau to pry it loose I could remove the pin. i was unfortunate that it was dusk and literally 3 million mosquitoes were attempting to make a meal of us. I think I ate about a dozen just breathing.