Perceptual learning is classically thought to be highly specific to the trained stimuli's retinal locations. However, recent research using a novel double-training paradigm has found dramatic transfer of perceptual learning to untrained locations. These results challenged existing models of perceptual learning and provoked intense debate in the field. Recently, Hung and Seitz (2014) showed that previously reported results could be reconciled by considering the details of the training procedure, in particular, whether it involves prolonged training at threshold using a single staircase procedure or multiple staircases. Here, we examine a hierarchical neural network model of the visual pathway, built upon previously proposed integrated reweighting models of perceptual learning, to understand how retinotopic transfer depends on the training procedure adopted. We propose that the transfer and specificity of learning between retinal locations can be explained by considering the task-difficulty and confidence during training. In our model, difficult tasks lead to higher learning of weights from early visual cortex to the decision unit, and thus to specificity, while easy tasks lead to higher learning of weights from later stages of the visual hierarchy and thus to more transfer. To model interindividual difference in task-difficulty, we relate task-difficulty to the confidence of subjects. We show that our confidence-based reweighting model can account for the results of Hung and Seitz (2014) and makes testable predictions.