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That's a valid concern, but it's pretty hard to find a good multiday route that stays close to an exit the whole way.My understanding was that there will be some people on the trip who are new to canoe camping and / or some with whom you have not tripped previously. If that's the case, I'd want options to cut out early on a trip in case someone was really struggling, the weather turned to crap or if the group dynamic was such that it ceased to be fun.
That's just me though... I can probably count on one hand the number of people that I want to be around 24/7 for 2 weeks.
I think you could easily stretch that route to 14 days if you wished and my biggest concern for the group trip that you've described would be the two long ports without any (legal) way to do them on separate days.
I agree that portages slow things down and, in his books, Beymer seems to cover a lot more ground in a day than I usually would. He describes the loop in 8 days while I suspect that 10-12 would be more reasonable and 14 might be downright leisurely.
That would also be a valid concern. I'm not sure how you could get up-to-date intel on water levels (check with the Forest Service?) but dragging boats through rock gardens is slower than portaging IME
Most likely, the club members, that sign up, would be experienced canoeists, but maybe not with anything like the Boundary Waters. But then, this route isn't typical BW.
I had no plans of going near the two lakes you mention, almost all of it is on the South Kawishiwi, and the only long portage is at entry point 32 One of my guide books recommends avoiding 32 and using the campground SW of there. Adds a little distance and some short portages.
I used the string method to get a rough idea of the length and came up with between 13 and 14 miles, using entry point 32. Add a couple more miles, if you use the campground. Way too short. So, I may need to rethink this, or do two short trips.