On the emojiis, there is already a TinyMCE plugin for emojjis/emoticons. You just need to add the plugin to the list of active plugs and then add the button. Contact your developer and request it.

I was looking today to see if the latest TinyMCE 5.7.0 can be a drop in replacement or not; depends on if they once again changed how the init is structured. I did read that I think old plugins might not work. Will, I do see that you have had someone to add the jbimages image upload and insert plugin to your toolbar.

I have added new toolbar sets to TinyMCE in Dolphin; should be the same method in Cheetah. There are a couple or more files; one is the file that defines toolbar sets with numbers 'HTML' => 1 (or 2, or 3 or ...); I forget where that is at the moment. Then you also have to go into ChBaseEditorTinyMCE.php and add your new toolbar set. Yes, this will require hiring a developer.

What Will wants may not be what Jenny or Joe, or Felicia wants. Asking Deano to make custom toolbars just for one user is taking him away from more important work when you can hire someone to do custom work. In fact, that is not the default toolbar set for the email compose; so you have already made changes.

It isn't clear what you are asking for here; I don't understand the arrows.

I was wondering today how much work it would be to be able to select which buttons should appear on which toolbar sets? Then again, it is pretty easy to do by editing the ChBaseEditorTinyMCE.php; of course that should be copied to the template and then changed there so it doesn't get over written during upgrades.

Show me an example of what your vision is.

What your seeing is tinymce, and it is modern. It's still in active development.