Look into calf sharing.
You could milk just a gallon at each milking and then quit once you have pulled that.
Then you put the calf back with momma and only milk again when you want to.
Depending on the breed, the calf will stay on momma for well over a year, keeping her supply up. And at the same time, it also grows the calf amazingly well.
Then you can decide if you are breeding the cow again and drying her out once her supply stops.
Then you just start the cycle over again.