Having paddled the Winnipeg River, I would paddle it again.  Just be careful to avoid private property.  That means paying attention to one's location, where one stops for lunch, and where one camps.  There are several provincial parks along the Winnipeg River, and they have campsites that are along the shore.  The dams all have portages alongside.  Some parts of the Winnipeg, particularly at Lac du Bonnet and Silver Falls, have summer cottages.