If you intend to use a motor most of the time, get a square stern. This has nothing to do with how simple it is to operate, because either way you'll get used to it quickly enough. It has to do with a side mount being another thing to deal with and get line tangled on.
As far as BWCA, if you get a heavy square stern canoe, rent your canoe when you do a trip up there.
4-place Boat Trailer
Full Size Sail Rig
Canoe / Kayak Anchors
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