I know modern CNC toolpath generators can be pretty complicated beasts, but I'm not sure to what extent they can use the sorts of constraints or tradeoffs you m

I know modern CNC toolpath generators can be pretty complicated beasts, but I'm not sure to what extent they can use the sorts of constraints or tradeoffs you mention to optimise their flow. The optimiser for a deposit-then-machine type workflow sounds even more interesting (and difficult). Is it worth printing those extra structures you're going to need to remove later? Maybe, if it means you can do some finicky machining operations in a different order later...