one time I wanted to write generic printers. E.g. printer of any type which support C++ iterators. But gdb can't call C++ functions from python api (excepting weird hacks like evaluating `print c.begin()` and catching it output). Although this is not very useful because most of types we use changes very rarely, that's why writing printers is only matter of time.
Another feature is breakpoints which sleep next N seconds. We have breakpoints which can skip next N triggering, but similar with time will be useful to me to debug mouse events in gui apps, etc.
Also the most new gdb still have problems with tab-tab completion (and even Ctrl-C don't return control immediately).
Also lately I often meet problem cannot insert breakpoint 0. Probably this is a bug, because answers from stackoverflow isn't relevant for me