This is similar to what I was trying to achieve with stealth sending, minus the denomination of receiving addresses. Usually users want to send to a pre-existing address, optimally DarkSend would be able to denominate the receiving party's amount as well. Stealth addresses allow you to generate infinitely many addresses from one receiving address.
Sadly, the only way to see if you have coins in a stealth address is to have the private keys in memory which destroys cold storage completely. You would not be able to see whether or not someone had sent you coins. Without stealth sending though, the master node would have to issue new addresses which cannot happen for obvious reasons. If someone can think of a way to fully denominate the receiving party's amount it would push the coin into complete darkness. When combined with Evan's I2P implementation Dark would be as anonymous/private as possible.
+1000.
This is the thing. It already seems to work this way. I've used DarkSend to send funds to a second wallet via an address1. When I try to see the balance afterwards of address1, I get 0, but I can see in my wallet that the funds have arrived. I'm trying to understand what happens so that I can get this flowchart to be correct!