This is the problem. A temperature sensor shouldn't be placed over any type of roof.
Agreed. Unfortunately, the station is where it is. His easiest solution is to move the extra sensor to the roof for long enough for the temperature to stabilise and then compare.
I find it difficult to worry over other people's station positioning, because mine is about 6'6" above the ground. Ideal positioning was easy when we had acres, now we have only about 1000 square metres, and there are houses and trees all around. I got the anemometer up about 7 metres, so it is pretty well in the clear. Unfortunately suburbia makes for problematic siting.