Hi,
In Mavericks I have seen this issue with a Bonjour Transfer.
it seems to be linked to my iChat 5 in Snow Leopard on the other computer.
Mostly I get "failed" items in the File Transfer window.
On the other hand I have had some like yours where the icon opens up the Quick Look window but this sometimes does not show the item properly (It looks like it will show and then does not).
I have found that this seems to relate to the size of the window/slide that appears and that dragging this larger does allow the pic to appear.
This Pic that did appear In-Line can be resized in the Quick Look window which in this case works.
But as I have said ,sometimes the pic does not appear In line as it should and the Quick Look window does not seem to "fit" the pic an needs Resizing.
As you can see by the button it can be opened in Preview.
If you resize the whole Main Chat/Interface Messages window does the issue change in any way ?
Normally pics automatically resize but I am wondering whether this is holding true at the moment.
8:49 pm Saturday; October 25, 2014
iMac 2.5Ghz i5 2011 (Mavericks 10.9)
G4/1GhzDual MDD (Leopard 10.5.8)
MacBookPro 2Gb (Snow Leopard 10.6.8)
Mac OS X (10.6.8),
Couple of iPhones and an iPad