Long time no lurk, but I just got back from MT/WY last week. Ran into the KSU Spirit Club of Jackson Hole at the Silver Dollar Bar and Grill, watching game 2 of the Bat 'cats vs. Oregon State series.
Sounds like I'm too late, but I'd be happy to try to help answer any Bozeman/Yellowstone/Teton/Jackson questions you might have as you live BBS this trip, SkinBen.
If you haven't already discovered this, camping might be a little tricky for you in Yellowstone. There are some sites that don't accept reservations, but it seemed like everything was pretty damn full. And it doesn't sound like backcountry sites are an option for you, is that correct? I'm not even sure they would give you a permit if you're by yourself. And if you're planning even a day hike on your own, use a bear bell, carry bear spray and be careful.
Yes, lots of people go to Yellowstone, but most of them are lazy and/or stupid and it doesn't take much effort to get to places were you have the place completely to yourself. Sometimes you don't even have to leave your car. Check out the one way roads just off the Grand Loop (Firehole Canyon Drive, Firehole Lake Drive, Virginia Cascade Drive, Fountain Flats Drive, and if they're open the Old Gardiner Road and Blacktail Plateau Drive).
As far as time to allow, if you haven't already moved on, we spent five days in Yellowstone and I don't feel like we even came close to "seeing it all."