Part of your idea solves an issue that has been bugging me for a long time. I have a generic "Downloads" folder, as I'm sure many others do. It's basically the staging area that everything gets dumped into before I decide where it should go. Some stuff stays in there indefinitely.
I'll end up with a lot of random installers, EXE's, documents, images, etc. Like right now, I have an anonymous setup.exe file. The file properties tell me nothing. It has a digital signature that says it's from Microsoft, but that's not helpful and not everybody signs their stuff. The only solution at this point is to run it. UAC is able to tell me that it's VSTS 2008 Database Edition GDR. However, sometimes installers take a while to get started to the point where you can see what they are and kill them.
I've been plagued by the same sort of scenario more times than I can remember. So, your idea presents a very cool solution. I can see an explorer extension that adds a "WTF is this?" context menu item. Or something that can store descriptive metadata locally.
I think a wiki/moderation model is a good start, but could run into problems. There are numerous threads here on C9 that hash (
) over various methods for ensuring the quality of the forums, reducing spam, mitigating trolls and knowing who to trust. I think some of those discussions might be obliquely helpful in figuring out how to make sure that the contributions were of high quality. You're going to have to dig them up yourself, it's late and I'm lazy.