Tom -- OK, I looked at your Schedule, Route and Lodging. First, here are some general comments. I was one of many college students (U of I) working in Yellowstone during the summers, and by the time I left after Labor Day most of the college work force had departed. That means that after Labor Day facilities such as cafeterias, general stores and some lodging start closing, especially at Canyon Village (almost 8000 feet elevation) and Lake/Fishing Bridge (7700 feet elevation). You should be OK until the end of September, but I would just be aware that not everything will be open.
Another general comment is the weather that time of year. We, the Savages (workers), celebrated christmas in Yellowstone on the 25th of August and some years it snowed a little. (The tourists were called Dudes.) However, the roads should be OK unless the road at Dunraven Pass (8859 feet, between Canyon Village and Tower Falls/Roosevelt) has not be cleared in a timely manner. Of course, rain/sleet is a more likely problem with the sunrise temps near the Freezing Point and the afternoon temps varying from the 40s to the 60s. Tent facilities would likely be frigid.
A final general comment is that I find the most beautiful and spectacular part of Yellowstone is the Grand Canyon of the Yellowstone with the associated Upper & Lower Falls as seen from Artist Point (SE side) and from Lookout Point & Grand View (NW side), all of which are very near Canyon Village. And, my favorite beautiful spot in the Tetons is the road along Jenny Lake, where the spectacular view of the highest peaks is the best in the morning.
With those general observations in mind, let me address the POIs for your chronological route, as well as a few lodging suggestions. The route from Jackson to Colter Bay will hopefully take the scenic road along Jenny Lake, arriving there by noon for the best lighting of the mountains rising sharply and immediately from the far (west) side of the small lake. A great stop for lunch.
The route from Colter Bay to the YP Lake/Fishing Bridge area should allow time to see and go in the famous, old Lake Hotel (check out the history), as well as standing along the side of the iconic Fishing Bridge where the lake flows into the Yellowstone River. That river is one of the few in the U.S. that flows north. Lake Village and Fishing Bridge areas both have cabins and are fairly close to each other. The Lake Hotel per se is pricey.
The route from Lake/FB to Mammoth might be too much for one day because the Canyon Village area has the most spectacular scenery in YP, a great walk down to the Lower Falls, and some good cabins to overnight. Heading north into the Canyon Village area, first take the Upper Falls road (right turn, East) and go 1 mile to the end to enjoy the view from Artist Point (short walk). Next, return to the main road, continue north 2 miles, turn right on the road past the small village (which becomes one-way) and go 1 mile to 1.5 miles to Grand View and Lookout Point on the left hand side of the road. Finally, continue on the one-way road just over 0.5 mile to the trail to the Lower Falls. If you all have good knees, you will not be disappointed by walking down the paved but somewhat steep trail to the very top edge of these huge Falls with the roaring sound and mist. This is my Niagara Falls in a wilderness setting with a gorgeous, dramatic canyon.
The route from Canyon Village to Mammoth goes through Tower Falls (another trail, under the Falls, but definitely a lesser attraction than the Canyon area). When you reach Mammoth, you can turn left (towards Norris and Madison) and take the very short side trip to the Upper Terraces of the Mammoth Hot Springs. Neat but possibly a lesser attraction than the numerous paint pots, hot springs and geysers from Norris to Old Faithful. The old Mammoth Hot Springs Hotel is worth going inside, but the rooms are pricey and primitive. A better choice for lodging is Gardiner, MT, just 5 miles from Mammoth. My son Mark and I spent a week at the Best Western (river-side room) in February 2009. (Darleen hates the snow & cold and did not want to go.) If you ask the locals, they will recommend some good but inexpensive places to eat in Gardiner.
The route from Mammoth to Old Faithful first goes through the Norris Geyser Basin, which is interesting but only if you have time. There are some neat rapids (left hand side) along the road on the way to Madison. Five to ten minute stop. Madison to Old Faithful goes by three geyser basins: Lower Geyser Basin (Fountain Paint Pot), Midway Geyser Basin and finally Upper Geyser Basin. Most require some significant walking but it is flat. At Old Faithful, one does not want to miss the famous, iconic Old Faithful Inn, which is not to be confused with the newer, mundane Old Faithful Lodge. Must go inside for a quick look and walk up to higher open floors. Open to the center fireplace area. I believe it is the largest log cabin in the world, but I have not checked the claim. The cabins associated with the OF Lodge are a good place to stay.
Tomas, the YP Savage