I have several cameras. But I did not acquire them for the purpose of "upgrading".
In my own assessment, my skills are far behind the most basic and primitive of my cameras (NO, I am not talking about digital cameras - perhaps digital cameras are different - not aiming to start another digital versus analogue war!).
I have several cameras because they allow me to do different things. For example, a rangefinder to do low light photography. A SLR to do macro and close up portraits.
But I have no need to "upgrade", because the cameras I already have can do ALL that I can ever want to for the kind of photography I am interested in, and which I do, and that is is traditional black & white photography.