When I browse forums and other sailing websites, I often see questions about stepping masts on different sailboats. Generally, stepping the mast on a trailerable sailboat or a sailboat under 28'.
So I have looked around the internet and found a few videos that show different ways to step a mast on different boats and have posted them here. If you have a question about stepping the mast on your boat email me at firstname.lastname@example.org.
Here is a great video of a gentlemen stepping his mast on his Catalina 22, he goes into good detail and describes it well. This should help you understand how a system can be arranged to make stepping the mast an easy process.
Here is a good short video of someone lowering his mast on his Capri 18. With his block and tackle system he makes it look so easy!
Here is a great video (or two videos really) that explain how to lower the mast on a Catalina 25 while underway in order to go under a low bridge.
The first video is the the process of lowering and raising and the second video is the hardware that is required.