normhead posted in the 300mm lens club considering results from stacking tc's with the DA* 200mm f2.8. Results I thought were pretty impressive ( think the pics are now missing from the actual post), that is a sharp lens.
cooltouch posted
a thread on mflenses where he stacked successive tc's on his tamron 300mm f2.8. His main conclusion was that the increased magnification did pull more information from his subject: a small panel with writing on it. Previous posters have already remarked on whether cropping is a more effective way to go; along with that using eg a pentax Q or toher small sensor camera with a suitable lens gives huge 35mm equivalent focal length (~ 5x crop factor with Q) and could be a way to go. I can add that the subject is important. IME wildlife, for example, cropping tends to be the way to go, upping the focal length and therefore also F stop and therfore much slower shutter speeds magnifies all the difficulties with extreme telephoto photography: vibration, shake, subject movement. And I find that fine detail is also compromised more quickly with tc's. However subjects like ships, where a very stable setup can be used, can benefit from the inherent increased info that cooltouch demonstrated. Atmospherics, however, can often be the limiting factor in such long distance photography regardless of the mode.
In any case, if you want to try the tc route, the lenses mentioned are the type whch will work best.