I've been continuing to fiddle with this since my post on April 3, 2020. I've spent a couple of hours on the phone with an Apple engineer (who reproduced it on his machine but otherwise no help) and hours since then fiddling.
It does now work for me, but is really finicky.
Here's what I think I know:
- The virtual touchbar (VTB) does not mirror the physical touchbar (PTB).
- The VTB is attached to the most recently used app that's displayed on the Sidecar. It continues to work, even if that app is not the active app, which is really weird.
- The PTB is attached to the active app -- unless that app happens to be the one running on the Sidecar, in which case the app-specific part of the PTB is blank.
- The VTB is most reliable if the app is moved to the Sidecar using the app's Window -> Move to <iPadName> menu option, although it sometimes works if you drag it there, too.
- The VTB is most reliable if the mirroring menu (enable in the Displays preference panel) says "Mirror Sidecar Display". Note that just because you have Sidecar connected doesn't mean that this menu item shows up. Furthermore, unchecking "Use as separate display" doesn't cause that menu item to be immediately unchecked, nor does it necessarily cause "Mirror Sidecar Display" to show. Using Window -> Move to <iPadName> seems to encourage the "Mirror Sidecar Display" option to show up.
- Using the "Arrangement" tab in the Displays preference pane to put screens where you (virtually) want them to be is really finicky for me. I now try to avoid it unless I really can't stand the arrangement.
Once I got it to work again, it didn't often revert back to its unworking behaviour for me, so the above isn't completely tested. Hopefully it works for you.