There is actually a whole paper about this by Roger Dingldine: http://www.freehaven.net/anonbib/cache/usability:weis2006.pdf http://www.freehaven.net/anonbib/ca

There is actually a whole paper about this by Roger Dingldine: http://www.freehaven.net/anonbib/cache/usability:weis2006.pdf http://www.freehaven.net/anonbib/cache/usability:weis2006.pd... Basically, you're more anonymous the more people use Tor, so increasing Tor's usability increases it's security.