Well, if someone wants to access your files, where there's a will there's a way. However, the likelihood of running into one of these guys (where they spend months trying to figure out what you used to have on the laptop) is far smaller than running into malware, keyloggers, trojans etc. online.
All you really need to care about is that the files aren't blatantly in a folder somewhere in the OS. Usually reinstalling the OS on the partition is good enough. You can also consider using CCleaner and using the "wipe free space" option at least once or twice.
I know some people go as far to reinstall a clean os using the recovery image a second time after the wipe.
To be honest, most people are not tech savvy. As stated earlier, as long as the file isn't blatantly available to access in a folder on the desktop, have access to your browsing history and auto fill info in the browser, it's generally fine. A clean install is probably more than adequate to hide the info, but I'm sure using a "wipe free space" of some sort would be able to provide additional peace of mind.
For the record, I'm pretty sure this is what Futureshop and Bestbuy charge $50-$75 bucks for this "service" when you buy a display laptop, so I'm sure it's more than adequate.
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