There's other guys that are real experts, but I'll see if I can help a little. I can't see your cam tree, and my software is different (pro). Start by making the outer profile line a dashed line. Then be sure that your geometry is all connected and trimmed, so you can chain select the bosses/islands completely.- as a chain. Then I'd use a pocketing command. I chain select the outside profile first, then select each of the bosses/islands. Then be go through the rest of menu. My apologies if you know and have done this already.