Hi,
IDN if you saw my old propose in “Outliner” thread, I made a small addon to illustrate missing features, but it seems it will be as addon for a long time until some one made a patch.
Added: checked, I’m pretty sure you saw it.
If you need just some of that menu entries, I can change it for you.
About Outliner features, as I know, it only possible through new GSoC projects.
About automatically select children, it’s a bad idea.
For me best solution is select parents in outliner by holding shift or ctrl and with dbl-click on last selected object you select all children objects.
Like a Collection behavior with shift hold and dbl-click (but it also works only for one collection…).
Outliner so inconsistent…I hope it will have some love next summer with GSoC.