if you start getting a lot of punctures
if there is a flat section developing along the centre of the tyre
if they start getting cuts and full of flints etc
if they get a ‘buckle’ because one of the inner threads has gone (this is rare)
if you see a storming bargain 🙂 but remember that life is too short for cheap road tyres, if you come off then the speed is higher and landing on tarmac hurts more than soil/grass
Mileage depends on the tyre make/model, the tougher tyres last longer at the expense of grip and weight…