I do not go through gates, period, except where I have talked to an owner and told that I can, and guaranteed the dog will not be out. A swing driver doesnt have that luxury, dont go through a closed gate. If you can bag it and put it over the gate, I will do that in the dark. I dont go to back doors, in the dark unless well lit. Or I know its safe there. There are a lot of safety issues related to not knowing an area, to being a swing driver, and its not worth the risk, especially after dark and depending on the neighborhood.
This time of year, if it looks like a gift and nowhere to dr, I may call the number on the package, if it looks like they are home, and I cant get to the door. But you really shouldnt have to because the consignee should know it is coming, and should make access available, you have to put some responsibility on them, to make sure sure they can get their stuff. Usually a delivery notice lights up a house, the next day.