Can circuit be split at transformer and run in two different directions?

I've been using this type of landscape lighting for about 20 years. All I do when I want the lights to go in different directions, I just hook up two cables to each post. There should be enough room as long as you twist them together before connecting them.

Although this item is no longer available on Lowes.com, the answer is still helpful for other kit options. The best option to support lights on different sides of the house would be to have a transformer with more than one terminal. This would allow you to run two separate wire lines to each side of the house and connect them into the multiple terminals of the transformer separately. Otherwise, the option would be to split the wire which is never the best option but is an option if done properly.