Interesting conversation going on here.
My personal experience comes from the gs500f. I purchased it a little over a year ago. I took the MSF class and I put countless hours around the neighborhood. This includes several chases from the local canine patrol as I practised. This month I finally upgraded to a Honda CBR1000RR. Great bike and I love it! It is such a pleasure to ride. It is a very different animal from the GS500 but I’m slowly getting the hang of it. I went back to riding the neighborhood streets again and saying hello to my local canine friends as they nip at my heals.
Long story short, I’m by no means am an expert rider. I have a lot to learn but I also felt ready to upgrade. So far I’m glad I did and I’m enjoying myself.
I would suggest you upgrade when you feel you are ready. Good luck