Nesting in non standard shape.

Hi forum, 

1. I'm struggling with an idea to create nesting solutions in a non standard shape, Usually nesting operations input a rectangular form for the nesting base. I was wondering if there is a way to nest shapes into a custom form, for e.g. if I wanted to input a sheet of 4X8 plywood that already has some shapes cut out of it. 

Does anyone know if there is a simple logical way to do this, assuming that it is a regular function that I will use very often. 

2. In a similar operation if I wanted to give my nested shapes some flexible parameters other than rotation, for e.g. allow the shape to scale +-10%, would that be possible? 

Thanks, looking forward to some ideas for you guys!