I wouldn't recommend Cherry Corner to Allen or Tipton Ford to Reddings Mill. Not for someone of your experience with the family.
Just below Cherry Corner is a very sharp S-curve with a very low hanging tree right where the current is going to put you. It will take some very strong paddling and handling skills to avoid it. As stated, there is also the remnants of a mill dam that you will have to portage. And it is not the easiest portage. Not bad, but will take a bit of work. And plus, if it was so easy, ask Buzz why he dumped on this float. I am in big trouble now!
Getting to Reddings Mill will be very tricky also. Just below Gateway the channel splits and you must stay to the left and even there, there a couple of tricky jams that will require very good handling. After that you will run into a spot where the river makes its first appearance next to River Rd that has some huge boulders across the stream that will take some careful negotiations. And then after that, about a mile up from Reddings Mill, the river splits again. You again will have to stay left. But this time, the water gets really skinny. You will be negotiating twists and turns in a channel that is only about 2 canoes wide. Then, when you get out of that, just before the old bridge, you will have to walk your canoe over the natural falls. You want to stay to the right this time. Go slow! It is slick and very rocky. Solid rock with lots of pockets and drops.
If I was you, I'd do the Allen bridge to Limekiln like Buzz said. You have great access' at both ends, its only about 2 miles and very easy to float. The river will split on you just down from Allen and stay left. Take your time and enjoy it.