Lame_Wolf - 1:37 am on Apr 4, 2012 (gmt 0)

Would there have to be human judgement involved?

Not really. I once knew of a site where you could test your text. It would then give a result on how easy (or hard) it was to understand.

If you write grammatically correct, with little or no spelling mistakes, then expect to get good results. However, if your text is spammy, or reads like you're a Jerry Springer guest, then the results are poor. (eg: There ain't nobody here no-more)