TWS is a very friendly track. I've been to many Driver's Ed events there, and it is mostly wide open. A lot of the turns are banked, and none of them are off-camber, so that makes driving it easier.
There is really only one spot that can cause problems, which is after turn 2 (assuming the regular counterclockwise direction), if you go off the track on the right, and try to correct, you may catapult across and hit the barrier on the left. I've never actually seen anyone crash there, but I've heard that 911's, being Rear Engine, RWD, are most susceptible.
I guess the setup can vary by organizer, but the Porsche club always breaks it up into 4 groups (beginner, intermediate, advanced and instructor). Typically, these groups run their own individual sessions. If someone is too advanced for the group they are in, they move them up.
I haven't had a chance to race any other tracks, but I have been to some others to watch, and TWS seems a lot more novice-friendly. MSR in Fort Worth, with all off-camber turns, is a lot more challenging, based on what I hear from everyone who has done both.
As far as compressors go, you usually have to fend for yourself. I always bring a little dinky cigarette-lighter-operated one, which works fine. In general, you need to bring whatever tools you think you will need, since the accomodations in the paddock area are pretty sparse.
A lot of times, if you are in a bind, someone with the right tools will help you out, but you can't count on it.
Hope that helped.
George