Yeah, I think I have the timing right, I tried a couple of different ways. I can see the tx and rx blink rapidly on the double press and rx flashes a bit before the upload fails. I get the "couldn't find on port error". After that I notice that tx and rx blink rapidly again and it goes back to "breathing" as mention in the link.
One time out of ten I'll get a different error... I should have wrote it down, because I cant remember what it is now.