There do still exist places in the U.K. with milk deliveries and it seems to work pretty well. People generally leave out empty bottles in a basket with some dial set to request how much they want.
The idea appeals to me. It intuitively feels less wasteful (but plastic is very low energy to produce compared to glass and it might not actually be that bad to put plastic bottles straight into landfill), and I’m not sensitive to the price or particulars of the milk (except that it is milk and not some kind of white-coloured water). Maybe it would be too expensive still. Or maybe people would care too much about getting certain brands of milk.