Finder has a keyboard shortcut to open a directory within a save dialog like that. But you could also use AppleScript to do that, if you're so inclined.
Both of these methods are discussed in this thread which should get you going.
As for the wait, if there's no title then off hand I don't really know how you could do that (I'm very very new to KB Maestro myself, so not very familiar with all of the options available) other than just to add another pause after you've clicked the image for something like 12 seconds maybe, just to account for a possible delay.
Hope it helps!