I raise the mast with minimal help.
Get the shrouds on their proper place. Make sure the lines run back so they wont twist.
I have one of those elastic double ball things to hold the jib to mast at the bottom. Just one.
Have the pin ready at the front, I leave the drum on the boat so it is the top pin on the furler I take out.
I raise the mast up some and walk it back. It helps to have someone take some weight off at the back, but I can do it alone.
I get the pins in the mast step.
Double check that the shrouds wont twist funny at the hull and that I wont be in the way of the shrouds on the way up. Yes, I caught myself once!!
I walk the mast up.
I release the jib and have the other person put the pin in place.
Done.
Does not require a lot of strength really. It can be unwieldy so an extra person it there mostly for control and to help out when you do something stupid like not double check you are in the way of a shroud line.
Try not to make it more complicated then it really is.
FWIW, a 5 gallong pail is about the right height to keep the back of the trailer from rotating down when you get on the boat and the trailer is not hitched.