It is really grad that you’ve detailed your workflow. It will make the discussion easier and I also appreciate your general tone as it avoid flaming which comes up now and then when users from other EDA programs come on this forum gathering information.
As for KiCad, you have to be aware that it is an open source solution. Thus it is much easier to write programs that extend its functionality. So if you find KiCad lacking a feature, it does not mean that something can’t be done. Most likely you are not the first one with this problem and there might be an external tool available. Here is a good list of external tools available.
Note that when I say external tools this means externally developed (not by KiCad developers). KiCad has a plugin interface, so some of these solutions integrate with KiCad.
And as already mentioned, the biggest tool is the @maui’s stepup plugin for FreeCad.