After wiping your laptop and hiding the data on the internet, remember to generate some fake browsing history.
Even if they don't chuck you in jail as a suspected terrorist, having a totally virgin laptop will get you nailed for import duty at the very least. Touch is your friend so you can add entries backdated a couple of months.
A long time ago, in an America far far away, the company my father worked for bought Gateway laptops that specifically had removable drives and advised all employees to have a "travel drive" for when they visited countries that were ahem less than civil. Good advice never gets old.
F that. If it's really that much of a problem, wouldn't it be easier just to buy a used laptop from craigslist, or an asus ee? That way you're guarnteed to not have anything on there that you don't want to be seen, rather than worry you missed something critical.
paranoid much? If this is a real concern, why wipe your whole box? Just store your sensitive information online and scrub it before you leave? If you really really must secure the entire system, then create a image of it an upload it (S3 or whatever). Keep a second clean image for use when crossing the border. Swapping images is significantly simpler than re-installing from scratch every time.
After wiping your laptop and hiding the data on the internet, remember to generate some fake browsing history.
Even if they don't chuck you in jail as a suspected terrorist, having a totally virgin laptop will get you nailed for import duty at the very least. Touch is your friend so you can add entries backdated a couple of months.