The inverse branches are not unique, you might think there is no choice being made but picking the standard branch is a choice b/c I can always shift the result by 2π by picking a different branch of the inverse. The answer is not unique & the assumption is that the calculators are using the standard branch.

Of course, but the choice is standard and thus the answer is 9. I can define a non-standard sqrt(x) which sometimes gives the positive root and sometimes the negative one, and then sqrt(sqrt(16)) could be -2 or undefined (if I defined sqrt(16)=-4) but that's just silly - the only reasonable interpretation for what the calculator should show for sqrt(sqrt(16)) is simply 2.