1 -If properly tanned, yes raccoon would work, or any other tanned hides for that matter. In this case you would probably need to make a paddle strop out of it as the leather would be rather thin and would benefit in some additional stability

2-some of the old paddle strops aren't much longer, so I would say yes it would work if you didn't have anything else

3- yes and no. while urinating on it once would not do much. Some plains indians tribes did use urine to break up the protein fibers to make the leather more pliable by soaking it in urine. however they still used fats and brains to make it soft. The ammonia in the urine also served as a bleach.