@nobhdy,
Reading through this, I suggest that the difference rests on different views of 'whats going on in the mind'. Kant has a view of 'subjects contemplating objects, whereas for Heidegger this is not the primary mode of 'being'. Thus Kant might have a view of a 'hammer', say as
representational of a stylized category of objects called 'hammers', whereas for Heidegger what matters is the action....
the intention to hammer. So for H, what K might categororize as 'rock' could fulfil H's intention to hammer, in various contexts. For H 'a rock' can be 'a hammer' but not for Kant. This is not to say that H has no concept of stylized objects, but that contemplative mode is secondary to the primary mode of dealing with the world.