All good advice Dave, as usual.....
I remember one trick. When the center board is being put back into position in the trunk a person has to be inside the boat to thread a large bolt into the s/s U bracket that retains the board in position. It will be very difficult to position the board, bracket and bolt in alignment to thread the bolt back in.
The solution is to use a piece of threaded rod about 18" long into the bracket before starting to put the board back in the trunk. Then offer the board up into the trunk, positioning the threaded rod through the hole first. The person inside can use the threaded rod to get the bracket into the right position.
When it is all lined up remove the threaded rod from inside the boat, apply lots of sealant and thread the retaining bolt into the bracket.
If you can have the yard lift the boat at the end of the day and you can have the evening to work through this, otherwise it can be a bit stressful with the clock running.
If the boat has been wet slipped in salt water the bracket or axle pin may need replacement, so going straight to stands may be easier and cheaper.
As Dave said it may be hard to get the board out, there may be some sealant around the bracket up inside the trunk (also this needs to be cleaned up before it is reassembled). So it may take some wiggling to get the board out. Using the threaded rod on the inside of the boat and taping it with a rubber mallet would help.
The uphaul for the rudder, will only take a few minutes, there should be a block inside the rudder post to give 2:1 advantage.
Bob