Currently, I’m using GNU Privacy Guard  and Veracrypt  to protect sensitive information on my hard drive with a password. A password that is only 7 characters long is usually considered much too weak to be of any use. Any law enforcement official, any spook and any cyber criminal worth his salt would be able to open the file in question faster than it takes to spell NSA.
I wonder if there are tools that check a number of files for weak encryption (using, I guess, a brute force approach) and if they find one, open the file. And the question which is even more important: If these tools do exist, how prevalent are they?
My security scenario is this: The aim is not to protect against an expert attacker who knows that I have encrypted files and who wants to gain access to those files. I’m thinking more of a nosy individual who happens to stumble upon a discarded hard drive and who checks if there is anything interesting (documents, pictures) but who will not put in any more effort once he realizes that there is only (what appears to be) random binary data.