If you cancel upon reaching VFR conditions you haven't operated VFR-on-top,
so why do you find that a "to VFR on top" clearance is easier?

Excellent question, and I would like to know the answer. If I ask for
an IFR clearance to the next way point just to pop up, I just get asked
what airport my destination is and then told it will take a while to
coordinate. If I ask for a clearance to VFR on top to the next way
point, the clearance comes right out. So, I agree, why is it different?

-Robert