Here's something cool I found, though it's designed for "shrinkwrap" boundings and not boxes:
http://cgm.cs.mcgill.ca/~orm/rotcal.htmlWhat language are you using? I'm thinking about writing some code to allow for a flood filler that won't work if an object is open (spilling out to the edges of the screen). It's for a paint program that lets multiple people use one canvas.
