What the documentation means is that the conditional expression you give to the (if:) always yields a boolean. You can use any valid conditional expression, even ones that compare numbers.
In your particular case, you're looking for something like the following: (uses the appropriate Harlowe operator)
[[Continue.->Three out of Five]]
(if: $Weight is 1)[ [[Give Avery the paperweight.]]]
Details: The = operator you attempted to use is a JavaScript assignment operator and the equivalent of the Harlowe to operator. If you really wanted to use a JavaScript operator there, then you'd want the equivalent to Harlowe's is equality operator, which is the == operator.