Dan
I live in a bungalow and have my wind sensor fixed to a redundant TV aerial mast which is fixed to a chimney which is about is about 30 feet above ground level. One thing you must try and do if you are siting at or near roof level is to ensure that the sensor is more than 5 feet above the ridge/apex of the roof, this is to prevent wind deflection from the roof, which will cause lots of problems with wind speed readings and temperature readings due to heat radiation from the roof covering.
I would only suggest using the pole provided if you can site it in an open aspect away from buildings,trees, or fences. Also your rain sensor should be sited in an open area.
Don't be afraid to ask that's what this forum is about, we all have to start somewhere.
Incidentally where do you live?
Alan