dottedquad

I would like a client to be able to upload an image, but only if the client has an active subscription. I envision a widget on the clients dashboard. When the client clicks the widget, they will be forwarded to an area where they can choose an image and press the upload button. The image would then be uploaded to a directory that I had already configured. After clicking the widget, and If the client doesn't have an active subscription, they will be brought to an area where they can purchase the proper subscription. However, I'm not really sure how to approach this. Can anyone point me in the right direction of how to accomplish this?