What information does PrivateSend conceal, and by what method?
PrivateSend conceals information about who the sender and receiver are for a given transaction (in the final sense). It’s the CoinJoin solution proposed by Maxwell, for the Dash Masternode system.
How do masternodes improve on the initial CoinJoin proposal?
The masternodes improve on the first CoinJoin proposal by making the total amount to be sent of the denomination, such that transaction anonymity is further increased.
In this system, the masternodes collects the coins and mixes them, rather than requiring someone to construct the transaction, which people can join.
Alice send some DASH to Bob using PrivateSend. Describe how an attacker could link their addresses.
If the attacker runs a masternode, they have the ability to observe the mapping, and can see the sender and receiver addresses.
In what way could PrivateSend be more risky than a normal Bitcoin Transaction?
When the masternodes are run by the people/organizations users wish to stay anonymous from, it somewhat defeats the purpose of attempting to stay anonymous.
These can be governments, insurance/data analysis companies, or acquaintances.