[luckylion]

That would be a very interesting project indeed. The fun part would be to hand the judge the syntax document and ask them to please "interpret" the licence according to these rules.

Slightly related, I wonder whether complexity/length of licences plays a factor in adoption. If you have something that is very widely known, somewhat short and readable by lay-persons, you don't need to check it every time, you figure out once that you're okay with working with XYZ Licence or you're not. If you'd have to essentially parse complex expressions of licensing fragments, I expect less adoption because of higher risk of catastrophic issues being overlooked (much like I'd probably not buy a candy bar if the store asked me to read & sign 12 pages of fine print to do so).

[Nasrudith]

It certainly does - I know when it comes to evaluating free or open tools the last to be checked are "custom licenses".