The only problem I see with this is that I have fonts like “MetaPlusNormal” which only has Italic in it's family, “MetaPlusBold” is a different font, which also has an italic version. So for text with MetaPlusNormal, and applying bold, character style or using CTRL Shift B still wouldn't do anything with the font weight, or add a bold style to the text.
A solution would be a brief dialog box, “No Bold Found – choose another font” or something, you choose that font, it creates the character style called something appropriate (or user defined) the dialog box could have a tick box to say “always do this”.
But now InDesign has to remember how all this works – this is getting complicated.
Dream on Euge, dream on.
Yes I've used the Tools that you helped develop. They are an excellent set of tools. I must look into them more, I'm sure there are lots of other things I missed.