It's great to see progress on this. Both PyPy and Py3000 have been just curiosities for me; a combination of the two is a very compelling case for making the move away from Python2.7.
You can use py3k with CPython, so there is no reason to make two jumps at once. It's like saying you might buy a Porche now that the roads are better. But you can enjoy nice roads without a Porche just as well!
Yes, but making a programming environment change involves a lot of disruption to your normal workflow. I agree that it's best to do it one step at a time in order to better isolate the problem when things go wrong, but I find it's also good to do multiple upgrades during the same period of time to maximize the value from the mental mode switch.