My observation is that when I've had to press harder to activate Hill Hold, it's because I'm on an actual slope and was already holding down the brake with some amount of pressure before the car fully came to a stop. On level ground, it activates with a light tap on the brake once I'm stopped. Do you notice any difference between activating on a slope versus level ground?
Hill Hold is behaving pretty well for me in recent updates. When it was first introduced, I couldn't touch the brake at all after coming to a stop without activating the ((H)), and subsequently accelerating from a stop felt like it was straining against the brakes for a split second before they released. However, I think Tesla has been refining the feature in some of these opaque software updates, and I barely even notice it's active anymore unless I look for the ((H)) on the instrument panel.