In my experience, conditional breakpoints are so unreliable, that I just dont bother trying to use them. When I need one I add code like

    if (condition) 
        print("");

I love debuggers but yeah conditional breakpoints are pretty bad. I tend to need to conditionally break when the same code is being called repeatedly with different inputs where only one of them causes the problem. The conditional breakpoint slows things down so much that I'd probably turn to dust before it ever actually halted execution.

And I work in C#, so I have no clue why there's no option to inject the condition and a call to Debugger.Break() and then have the JIT recompile the function live. It would actually make conditional breakpoints usable!

In my experience, they're not unreliable, but they do massively slow down the application being debugged. I often do what you suggest, except with __debugbreak() (which compiles to int3).