Claris CAD will do this when you group the dimension with the object. Associative dimensioning (also called Dynamic Dimensioning) means many things to many people. The most commonly understood meaning of associative dimensioning is that any change that you make to an object will automaticalyy change the dimension for that object. This is not supported in Claris CAD. However, dimensions can be selected or grouped with the object they dimension and will increase or decrease as you resize the object.
This is only strictly adhered to for objects in horizontal and vertical positions. For objects at other angles, repeated resizing will cause the dimension and group to drift apart at one end. This has to do with the fact that the bounding rectangle for a dimension is not actually the width of the object being dimensioned - rather it is the width needed to accurately display the dimension of the object being dimensioned.