I tried a Kenko 1.4TC on my Sigma 150-500 yesterday evening, which was sunny.
At 500mm the lens is f6.2 so TC gives a further 1 stop loss, but I still had full autofocus on my D300s. Also OS was working as well, very well in fact.
This is a combined focal length of 500 * 1.5 *1.4 = 1050mm
As the evening drew on I tried AF and it still worked, but with more hunting as light dropped. But on a tripod I reckon it should work well, I was planning on field testing the setup tomorrow - weather permitting. I'll try and post some pictures at some point of this setup.