Going tubeless is definitely dependent on your terrain. If you find you're riding smooth trails most of the time, and that flats don't really seem to happen to you too often, then you should be good. However, if your terrain is bumpier, with more rocks and possible debris, then you should definitely consider going tubeless. This is especially true if you notice frequent flats due to your terrain. You could find that switching to tubeless could end up saving you some money down the road in avoided flats. It is worth mentioning that it is possible to still get flats while tubeless, but it is far less likely to happen and much better for rougher terrains.