Just a thought that with the DA* and TC your starting to get up there in size and weight and still really haven't got much reach. I only ever thought of getting a TC to extend long teles to extremes where size and cost are extreme to match. If it were me, I'd get the 50-135 and the DA* 300 for the long shots
Keep your speed up & size down while maintaining maximum IQ.
OTOH, what I really did was get a Voigtlander 180/4. Its tiny, sharp, comparatively inexpensive and close-focus too. Depends on what you need it for I guess.