Why is it a mess?

This is essentially what happens in python: An empty string is considered false while all other strings are considered true. That's just sugar offcourse, you could do if mystring.length() > 0 instead of if mystring and get the same result, but it's a useful shortcut.

Considering integers different from zero to be true, and zero to be false is also very common although the same tradeoff applies if myint could always be rewritten to if myint <> 0 which does have the advantage of being more explicit.

automagick type-conversion like PHP have is nuts though, they consider "0" to be false because the integer 0 is false. (but "0.0" is not false, despite the fact that 0.0 *is* false.