As a petrol station staff veteran I never used to bother unless it was a scooter or a 125 and I didn't recognise them as regulars.
It is an absolute pain in the arse but needs to be asked otherwise if there is a driveoff there's a good chance its coming out of the cashiers wage or best case a severe bollocking for not following procedure. In fact if there is a drive off and you have followed procedure it can still end up a massive argument
The cashier is liable everytime they press the button on the till to authorise a pump. It is up to them every time to decide if its safe or legal to do so
If anything the main issue I used to have was people wanting to fill up anything other than an actual legal fuel can. Milk bottles, 2 litre coke bottles etc etc.
I also had a massive argument with a man once because I wouldn't let his (probably) 8 year old son use the petrol pump. Guess who would of been getting blamed if anything went wrong in that situation?