There seems no other way around it: If advertising is to be effective in the digital space, it is going to have to learn more about user behaviour online and tailor messages accordingly.
One critical question involves the degree to which privacy rights are tested in the quest for more sophisticated ad service.
This frontier is well explored in today's New York Times' Bits feature on the NebuAd service in the United States. It gathers information through Internet Service Providers (it has a roster of small- and medium-sized ones) and categorizes what it calls the more "innocuous" categories of sites surfed, then matches ads with the user. It alerts users they're being observed and permits them to opt out.
There seems to be some sensible boundaries in the mix: NebuAd doesn't know who you are or where you are or even that you are one and not two or three or more users (an IP address is used by an entire household, for instance). And it chooses to exclude certain categories --- health and sex sites, for instance --- from the ad-serving roster.
The implications are significant, no matter that NebuAd is attempting to responsibly play in this space. The competing interests of commerce and privacy are going to have a challenging time playing nicely, but without some commingling, it is even more challenging to see where the new revenue models will originate.