I feel like no matter how you denominate pools or break up transactions, we need something in addition to Darksend to provide even greater anonymity. Regardless of how you break up a transaction, blockchain analysis could still pinpoint where coins are coming from and where they are going.
I keep seeing this, but it's simply not true if DarkSend gets a high enough volume of inputs. All coins actually move in the final transaction once all parties sign, at the exact same time (because the master node broadcasts the finalized transaction). If we are using the 100 DRK pool, and there are 20 inputs to it and > 40 outputs, who sent what to where? It's even harder once the change is denominated and sent back to the sender. If 20 people all get change it would be very difficult to say who got what.
Expounding further, if you then use the fabled change pool, sure, all your change addresses move at once, but so do everyone else's who is using the change pool for that block. And this all happens at the exact same time, once again. Now, who owned the change addresses before they were mixed and which output address did they get?
It would be theoretically possible to lump change input addresses together by prior transaction number but who controlled the outputs would be unknown.