Unfortunately we have no control over how long it takes for the image caches at Gravatar and at Facebook to be flushed. We also have not control over which images Facebook chooses to display. We ahve no control over which image Facebook chooses to display and they make chnage frequently. What follows may ot may not be wehere they are at today:
Only the first five images uploaded to a post (direct inclusion/gallery/slideshow) will be sent to Facebook. The images size has to be at least 200 x 200 pixels.
To select which image will be used for things like Facebook Publicize, you can use a theme that supports featured images. If a featured image isn’t set or your theme doesn’t use featured images, then the code tries to pick the first image in the post or page. If no image is found, then the blavatar is used.