Hi,
I could say : after the first dormancy, generally for me.
For me it is more about root-mass than leaf-count.
As for watering, a tree needs more water than a cutting. The best way to know, is by letting the pot go (a bit/enough) dry in between waterings.
If you find yourself watering a liter (1/4gal) every other day ... you probably have a tree in front of you .
If your cutting is in an half gallon pot (2 liters pot), and the pot is full of roots, that you can slip the tree out of the pot and all the dirt stays together because of the roots ... you have a tree.
If you have one root running in the pot, that you have more dirt than roots, you still have a cutting ( that can die quit quickly is you're rude with her) .
Of course, hitting a bush and getting stems with half-gallon of roots attached ... is called getting a tree too in my books.