I usually fill until the nozzle automatically shuts off, then attempt to fill to the next even dollar. But that isn't really important except to see if I can do it.
Unless you are fanatic about the last possible degree of accuracy, it doesn't matter. Any irregularity between fill levels will average out over a few fills anyway. Usually variations in driving conditions (hills, wind, temperatures, traffic conditions) will swamp small variations anyway.
On vehicles with small tanks, such as motorcycles, a variation of a tenth of a gallon in fill levels will show up, but it will average out in another tank or two.
My Tundra and my wife's Outback both say to fill until the automatic nozzle shuts off, and not to try to "top off" after that. I think if one uses the slowest fill rate at which the automatic nozzle will latch, the fill levels will be reasonably consistent. In any case once a few tanks are averaged any small difference in fill levels will disappear. The only time I think I would try to fill as much as possible might be if I were setting out on a long trip across the desert, where availability of fuel might be in doubt.
Diesels might differ. Diesels don't usually have evaporative recovery systems, since the fuel isn't prone to evaporation. But if I were going to fill the tank and park the vehicle without driving far enough to burn the fuel down a little, I might worry about losing some fuel to overflow should the weather be really hot.