We still seem to have fairly bad tooling for advanced debugging use cases.

There's no good reason you shouldn't be able to have an IDE maintain a text overlay of debugging points which is solely supplied as breakpoint scripts to the debugger instead.

IDEs seem to conk out at click to set breakpoint.

That has literally been table stakes for Windows development since the 90s.

Not having the debugger fully integrated into your integrated development environment is strictly a problem of the commercial Unix and open source crowd and their "Real Programmers are fine with stone knives and bearskins" machismo.