I've lived in Middletown, NY (Orange County), Little Falls and Ilion, NY (Herkimer County) and am now back in Mamaroneck, NY (Westchester Couinty) where I was raised...

As far as where "upstate" begins...I think its anything north of White Plains or North of where the person talking lives...

though most people north and west of Kingston will generally agree that they are in "upstate" NY