Fast replacing/upgrading has been added.
For 1a (replacing a generic to reopen the UI), this is now possible, but because I had to do it kinda hacky it only works when building one at a time. Drag placing does not work. This is due to Factorio not actually letting you build on top of the same entity, so I had to trigger it on the actual button press.
Undo should work all of the time. When fast replacing it will deconstruct the generic chest and replace it with the normal logistic chest, or it will undo the selection and swap it back to a generic, when the selection UI was used. In that case, double tapping Ctrl+z will entirely remove the chest. I imagine there is going to be some weird scenario that I missed, so let me know if you run into any issues with undo.