1. Does he have auto insurance? How much does it cost?
2. Has he bought car insurance yet? If yes, how much did he pay for it?
Are these two sentences natural to say?
Thank you very much
I am not an English teacher, but I am a native English speaker so I will comment. All the sentences sound natural to me, although the last one would sound a bit more natural by saying "If so, how much did he pay for it?"