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I found that raising the mast singlehanded I cannot use the winch. The reason is that I need to be standing on the deck to keep the mast raising strut perpindicular to the deck and mast. The first time I raised the mast I was not watching this and bent (destroyed) the mast raising strut, as well as bending the fitting it pins into on the deck. I am 175#, but still find the effort to raise the mast is considerable.I use the following checklist to raise and lower the mast on my '99 26: RAISING MAST-make sure rudder uphaul rope is tight-unplug light harness before trailer enters water (greatly extends life of bulbs)-If raising mast in water, make sure ballast is added first.-apply spray silicone to mast crutch roller & bottom of mast to slide better-After mast is rolled aft, tape shrouds to lifeline to prevent buckling-Don't trust Jib Halyard stop alone to raise mast--also attach to winch and tie off (do this first and close stop second)-Pin Mast Raising Pole perpendicular to mast (won't pivot there from parallel)-Mast raising pole how many degrees forward / aft?-Tie forward end of furling jib to mast raising pole--keeps it from scratching the deck-before hoisting final check that mast is not binding in crotch-Go slow, don't be in a hurry, check each step of the way..-Main sheet and tackle should be parallel and straight-When raising mast use body and grip on main sheet as group to prevent mast raising pole From veering port or starboard; it becomes stable after raised 1/3 way or so, but needs this help at first.-Pull furling into bracket by tying rope around neck and stepping in loop on other end.-Do not leave boat with mast raised without water in it--wind can knock it over.LOWERING MAST-Insert mast crutch (bend towards front of boat) and pin.-Draw main sheet across cleat for friction-Steer top of mast into crutch by moving main sheet (slightly) sideways.-spray silicone roller & bottom of mast to slide better-Start slid forward from BACK of boat and work past harken hdw & etc., then (holding mast in place--very difficult) go to front of boat to finish.-Use mast raising pole to support furling jib base during transport.-Secure shrouds to lifelines with cable ties / rope (elec. tape leaves residue). Make sure shrouds cannot flap around and scratch deck.-Lash mast fore and aft for transport.-Tie stern to trailer 2x, secure rudder, tie bow to trailerNote: I've got Harken lazy jacks and a roller furling jib, which complicates the process, as well as the %^$#@! installers at hunter attached my mast plate crooked. Yep, visibly crooked, making for some interesting adjustments and workarounds to get it all up and running.email me at gsweitzer@voyager.net if you would like more specifics..