1. and 3. can be solved by checking "Object vertex against cloth polygon" and "Object polygon against cloth polygon" options in the Simulation settings dialog. 2. is more difficult. The best way is marking one single vertex as "Choreographed", it should be a vertex that must be grabbed by his hand. Create a primitive, position it close to the choreographed vertex on frame 0 (above the sheet), parent the sheet to the primitive (I suggest a simple sphere), and animate the sphere to go the hand of the rolling person - should be after 10 frames or so. THen let the primitive follow the hand exactly: the sheet should be dragged nicely! Tough job, you'll probably have to do some tries before you get it, but this is the way I managed some pretty neat dynamic cloth tricks. Oh, and don't forget to make the primitive invisible before rendering :) Hope this helps, Steven.

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