I have a few questions for you -
Could you limit the rectangles available to be entered?
How random do the positions need to be?
If you could give me an idea of what it is for, it would help - but I understand if you would rather not. If you want, I might give it a shot in PHP for free. The image drawing functions for PHP seem pretty simple, and that would make it web-based and os-independent. I really don't think it would be that hard if there is a decent limit on the rectangles inside (or the outer rectangle is a decent amount larger than the combined smaller rectangles).
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