In Liberia the subject on temperature and radiance effects on voltage and current is very interesting and confirm my believe that pole mount is better and lots of breeze. (especially not knowing how old is the roof and the construction)
Another thing I observed are the wire size and quality. Always buy AWG made in the USA and not elsewhere. It's a big difference!
A pole mount will make more energy because of the increased voltage due to lower temperatures than a roof mount with less airflow, that is for sure! But it is probably going to be not a whole lot. If the PV is 10 degrees hotter and the temperature coefficient of power is -0.44%/C, then we would have a 4.4% increase in efficiency, which could be overcome by buying 1 extra module on a 20 module array.
Also a good point you make about not having to worry about dealing with a rooftop leaking.
I also like how pole mounts look and how they can be easily tilted seasonally, but some people do not want to do the extra engineering to make the pole mounts stay upright.