I've done this once on my 27 once and I will never do it again! It took 4 guys and a lot of slow and careful coordination. A few tips if you are going through with it: tie a safety line to the outboard just in case it goes in the drink, if on a fixed dock wait till high tide so bending down is minimized, position the boat to maximize dock area, and tie the boat close and tight.
Good luck,
Manny