In a previous thread
on this subject (may be in archives), I suggested caution. The Law of Unintended Consequences may apply. As with a number of boat tasks that you haven't done before, the difference between theory and reality may be dramatic. If all goes well and as preplanned, this may not be a difficult task. But it could be scary depending on a number of factors, all of which could result in a LOT of water coming into your boat and could result in the need for an emergency haul out. My advice previously, and now, is not to attempt this task the first time with the boat in the water. Do it with the boat on the hard the first time and get a good sense of what is involved at every step of the way. After that, you may want to do this in the water and if so, you'll be a lot more confident of doing it successfully.