It's actually planes that make a "kaboom" because of the two distinct shockwaves (leading edge and trailing edge) whereas a detonation just makes a singe shockwave which we hear as a plain "boom"
It doesn’t matter, if the object is traveling faster than the speed of sound it breaks the sound barrier and when that barrier is broken a massive shockwave occurs called a sonic boom
To my knowledge, yes. It's because if an object is travelling, air molecules bounce off of it creating a pressure disturbance, which is the same as a sound wave in air.