This button activates the simulation after you set up everything in the Cloth Room.

The simulation is only good for one pose at a time, so you must run several simulations for several poses.  As for the 'sticking' dynamic clothing to a figure, that's what conforming clothing is for.  It is unlikely that vendors would create both dynamic and conforming clothing of one type, double the work for an item that might or might not sell. However, dynamic clothing can be converted to conforming with some work through the Fitting Room but there are no guarantees that the transformed clothing will behave the way you want when posing. 

 Another solution to consider is saving a completely dressed figure back to the Poser Library and running simulations in the Pose Room through the Animation Scripts from the taskbar.  Applying morphs to figures with dynamic clothing is easily done.  You need to have the morphs kick in during the simulation.