Building new roof on my house (need advise)?

Ok so here is the deal we have a pretty bad roof. The shingles are falling off from strong winds and cold weather. The siding is destroyed from squirels, birds, and racoons making holes and nest through them. Some parts of the roof are leaking. So here is my question to all those who are experienced, what brand of shingles are good? What type of siding is the best? What insulation is the best? We also need new plywood and beams so what would you reccomend? Basically its a 2 level house its location is near Chicago where we get long winters, alot of wind, very hot summers and losts of rain the spring. Also damn animals are always trying to find new places to make wholes. So if you can help me to find out which products are good and yes we do plan on keeping the house for a long time. budget is about $6,500 Thank you