In my teaching this often takes the form of a student who is trying to stretch a Googling expedition into a positive ID and ultimately a lot of sordid details about someone who is probably not all that well-known for their compromising behavior. There are many obstacles before the public vetting of the dirt-dishing can even begin:
1) People are journeys -- not destinations:
There are 34 Springfields in the U.S. Some people have that many alter egos connected to a diverisfied multiple personality portfolio.
2) The trails they leave -- they may bob but not weave:
The web is not definitive. Try circling back to sourcing one's virtual history or even a current web presence is not about closing loops or riffing on a central theme or obsession. There is no one trail or "go to" site for intimating where the next detour digresses or the former backroad resurfaces as an eighteen lane interstate.
3) The web is more effective as a communications medium -- not a research tool:
It's easier to talk up a potential ally than track down a potential social menace. Making a professional connection is more reasonable than trying to corner a criminal suspect.
So how do we get away from using the web to track a fixed target the way a P.I. stakes out a parked car? Part of that realization is the expectation that cases are not cracked by keyword searches or even traditional document retrieval but by reaching out to potential witnesses, experts, and stakeholders. But before those overtures are made? First lay the groundwork with sound research practices.
That said, more incriminating evidence can be found every day. What turns up expands our notion of an increasingly transparent public domain. We see this as the digital natives begin to outnumber digital immigrants and share personal details in a way that would startle their guarded elders.
But is it us immigrants who are exposing our naivete when we complain about privacy invasions and storm the switchboards of the institutions where an employee's laptop is in breach? Perhaps yesterday's healthy precautions are tomorrow's unfounded paranoias. This is the luxury of the self-important. Should a budding investigator be hot on the trail of some middle manager for their next homework assignment? They may not need to keep a low profile. Because the profile cut by the target in their sights may dip even lower.