A) There is no Stupid Questions... only stupid answers
B) It wouldn't matter how cold the air is once the engine is up to operating temperature and the supercharger is hot... the temp going into the engine will be the same unless you get an intercooler.
Think of it as the supercharger is generating heat by spinning. Say under normal driving the SC is heated up to 150* so the air going thru the charger will be heated up to a certain point close to that. No matter how cold the air is, once it gets to the supercharger it will be heated up to the same point. This is why we have the reports of dyno testing HAI va CAI... the differences were not worth the extra money it takes to try and get the air cold. Just get an intercooler.
This is also why we refer to them as Heatons