Yes it is possible to calculate the pitch from photographs provided there is enough information available, i.e. the view of a gable end for instance. A hip roof would be rather difficult though.
Your second sentence does not make any sense. You do not increase the upstand when you reduce the pitch, rather it decreases.
On a 45 degree pitch, the rise and the going increase equally. So if you were to measure out 6 feet from the angle then the rise would be 6 feet also.
However, on other pitches you would need to use a bit of trig' to sort out the rise and/or the going.
If you know the angle then use tangent on the angle and multiply the figure given by the going and it will give you the rise.