The answers to these questions depend on a huge number of factors. Extra flotation is usually a good thing. The general rule of thumb is that you should deliberately capsize your canoe on a warm day in shallow water near shore at least once to figure out what recovery techniques work best for you. The large float bags commonly used in white water play boats could clearly help. It is also a good idea to have someone with a motor boat who will keep an eye on you and come out if you need a hand. One of the advantages of a sailing canoe is that you can often sail them full of water, bail them out, or simply take everything down and paddle to shore if you have a problem. Your mileage may vary,
I have to work that weekend unfortunately and will not be able to run their sailing program this year as I have done for the past few years. It is not clear if they will be able to find a replacement. I do plan to attend the WCHA assembly in July so that might be a better chance to meet.