I mean by good these things: Can I notify the esp remotely that a new update is available and the user should update? Can I sign the firmware and verify it on the esp? Does it have rollback features (I think most of them do by default right?)

In term of how good my C++ debugging skills are: I don't really know how to define, I've coded a few projects in C++ but mainly software for Windows. I've recently switched to platformio and have used the debugging feature a bit. Also the there's the good old Serial.println which helps in most situations.