Most of existing computer-based diagnosis systems for the functional disorders of the upper limbs tend to be unintuitive as they are based on the static tasks, and the assessment criteria are limited to motor capacity. In this paper, we suggest an intuitive assessment environment for the upper limb disorders using generic haptic devices and a pulley metaphor. It aims to assess not only the motor ability but also other abilities like the problem-solving ability. The task scenario for evaluation is that a user should move an object to a specified location using the pulley, and the weight of the object is controlled as a manipulated variable. Also, to establish the valid assessment criteria, we explored some variables that can affect the elapsed time on each task with the user evaluation and statistical analysis. From our experiment, we found that the weight of an object affects significantly on the elapsed time. Moreover, the time duration of keeping a grip and the frequency of shifting the movement direction can be additional assessment items.