I think you may be able to use the ResetToBootloader() function in the C++ inserts, which is a feature on this version of Oopsy. We unfortunately don’t have documentation for it at the moment though.
I do remember a community member trying this out, but I couldn’t find the thread right away.
Edit: I just found them. This thread should give you an idea of what the C++ inserts look like. And this is the thread where a community was working on adding ResetToBootloader() with custom inserts.
Using an ST Link is another option for skipping the button presses if you can add another USB port to your project.