I don't run TS2009, but have seen this in TRS2004. The bogey/coupler file *.jpg images may not be associated correctly with the files that "call" it. OR, possibly, BOTH coupler and bogey *.jpg files just might be missing altogether. In other words, the bogies and couplers have the *.im files, but no *.jpg image to paste on them.
You will most likely have to manually repair these assets or locate similar bogies & couplers.
Hope this helps some.
Al