Hey Jesse,
See this:
Drag Finder selection to "Found Image" in Chrome Browser window - #11 by ccstone
Note that Gmail in Google Chrome will accept pasted files in outgoing messages now.
Pasting is more efficient than the drag and drop method in the thread above, so take a look at this:
Open File Within an Email or Application - #8 by ccstone
You can put one or more files on the Clipboard that are then available to paste.
User an Execute an AppleScript Action to run the given script.
Get back to me if you need help with it.
-Chris