@justastatue Wow! Great response and lot’s of added thoughts 
I do agree with almost all of what you said. Especially about the potential of the Active Tools. Placing the Tool Settings into the Toolbar instead of the Sidebar could also be good but also might clutter the Active Tools themselves. I guess this needs a design proposal.
But one of the issues of the Toolbar is that the definition of a “Tool” may vary based on the task and workflow. I can confidently say that any animator I know would never touch the Active Tools, even if they improve their functionality and accessibility. They will always be slower than the default operators and they take away space for actual animation tools, like the pose library, rig controls/properties, selection sets, etc (These used to be in the Toolbar in 2.79).
Tools that have bigger UI’s that won’t fit into the current design of the Toolbar and will never be Active Tools themselves.
I do like the idea of bringing the redo panel and the tool settings closer together and bridging the big gap between the operators and active tools. Right now they are 2 completely separate but very similar systems.
The big difference between them as far as I can see is that the active tools get their settings defined by the user before they are executed and operators have it the other way around with the redo panel. Apart from that there’s the difference that operators are executed upon using the shortcut while active tools are instead switched to with the shortcut and need extra mouse clicks for executing.
I even proposed a small visual change to try to bridge the 2 but there needs to be more to it to bring them closer together.
(I might need to change the name of that thread to “Bridging Active Tools & Operators” or something)
But I think the bridging of the Active Tools and the operators is a separate issue and improving the interface to provide tools (not just active tools) to all users is what I’d like to talk about here.