California Live Oak is difficult to say the least for me so far. Put it this way, the one I collected back in Feb. may be dead, and had some roots, and I was very careful. Some say they are easy to collect, but I have never had any success with an airlayer, cutting or a dig so far, we will see. People say airlayering is iffy and cuttings are a nogo and that has been my experience as well. Even the recent rootwork on the young tree I have been raising for a few years seemed to revolt into dormancy as the buds were popping. It seemed to tell me to just go $#@% off for trimming it's lankey roots back half way.
I'm probably timing it wrong and just need to figure it out, like you, trial and error.
Give it a try and try to remember the bud state each time when you attempt to airlayer or take a cutting and who knows.
Good luck