Re: Degree of difficulty in circumnavigating Lake Superior ?
It can certainly be done with your boat. Just pick your weather windows wisely, and on those long runs plan for weather to change for the worse.
If you are willing to sit out bad weather on the lake your biggest issues are: Keeping warm, keeping warm, keeping warm! Superior does not warm up much until mid to late June, and warm is a relative term. There is not much colder than a night aboard in June, where the day has been sun and 80 degrees, and it goes down into the 30's at night.
Good Luck, and have fun. It is beautiful!