Fresh no oil;
Add a pint to the oil filler hole to fill the troughs and 3 through the door to oil the bands. Start and run till up to operating temp. After stopping open the top petcock and let any extra drain over night.
If this is an oil change I leave the drain open and run a 1/2 pint or more into the oil filler and let it flush and drain the troughs put the bung back in and add 3 1/2 pt through the tranmission door then check the top petcock.
Four pints won't be enough. It takes four quarts. As for oiling the bands, they should soaked in oil before they're installed, and the other transmission parts should be oiled when they're assembled..