I recently pressed my first cheddar and got a rough surface due to the cheesecloth sticking slightly. Is there a good way to prevent this and achieve a smooth surface?

Cheesecloth should not stick to the surface of the cheese during pressing. It will do so if the cheese dries out too much during the time in press, and there is no way of recovering from the damage. So make sure the cheese stays moist whilst it is in press, using 5% salted water, at the same temperature of the cheese, to keep the cheesecloth moist, if whey does not do it. The cheese will not absorb the moisture.