> considerably more expressive

is that an advantage? Do you have the time to explain this a bit more?

I feel that new users need less expressiveness, to avoid decision overload, and keeping one automatic directory save point is easier to mentally manage than a stack of them.

I do recommend using pushd/popd in shell scripts (always) and interactively (if you must), but I think 'cd -' should be the first thing you introduce to newcomers w.r.t tracking working directory changes.