I would tend to agree that except for wind, the rooftop location is not the best for either temperature or rain catch.
In case you do decide on the roof mount, here is the way that I installed my VP2 wind set. I have the ISS on its own tripod at ground level. (the advantage is being able to split them)
I was also apprehensive about going onto the 2nd floor of either my previous colonial house or my current 1½ story. I was however, comfortable about going on the lower roof of the garage in the first case, or the addition area on my current house.
I'll attach pictures of both my current anemometer mast installation and my old house setup. I have the two legs mounted so that the entire mast can swing up or down. The side bracket gives extra support and anchoring. This works well for maintenance. The mast swings parallel to the upper roof edge. Since the resulting wind mast direction was not "North", I correct for that in the consoles.
You will need to make sure that the mast extends sufficiently above the upper roofline. I believe that mine does. The new setup with the dual wind set has heavy-duty Rohn masts collapsed to form a double wall. This extends higher than my old house. There is some slight sway when we have winds >30mph, but it seems pretty solid.
Current setup:
Prior house installation:
Greg H.