I cannot give an estimated time, there are too many other factors.
I started to look into this. One idea I had was to add a function where you right click an existing named keyframe and do "Set as preset X" or something like that. Then I realized that instead of having just the name of the keyframe we could save all the data associated with it and use *that* as a preset maybe. This way you can add a rich keyframe with some pre-made drawings in one click. There is also a feature for keyframe "color" that would fit nicely into this.
So now I'm thinking that instead of saving this as a list of names in the preferences, it might be simpler to have a "preset KVA" that is a normal annotation file but containing many presets for keyframes and drawings. I think this could simplify the logistics for the more advanced automation scenarios. In the preferences you would point to your preset file, it would analyze it and then for each shortcut/action slot you would select the thing to add based on what's in the file.
edit: scratch that, it would be too complicated to setup. I'll stick with simple name+color presets.