For me the biggest issues are to make sure I have a good mast-up crutch that mounts in the rudder gudgeons and making sure I have the shrounds lying in such a manner that they will not bend turnbuckles during the raising process.
I learned about 15 years ago that finding a good hill is a huge help. Park near the ramp on a hill with the bow down-hill. This raises the mast closer to "vertical-with-respect-to-earth" and when you get the mast vertical, it will fall forward to "vertical-with-respect-to-the-boat" and stay there while you attach the fore-stay.
Taking it down, I use the jib halyard as a brake. Connect the halyard to your pulpit, take up the slack and use it to control the fall of the mast as it comes down.
