It depends on the amount of zoom you are using. At the 55mm end, it isn't going to matter a whole lot, even in relatively dark conditions. Image stabilization is designed to counteract camera shake and the amount of impact that camera shake has on your images is directly dependent on two things, the focal length and the shutter speed.
If you are shooting with fast shutter speeds, you are unlikely to have camera shake issues at anything but the longest focal lengths because it can capture the image so quickly. As shutter speeds become slower, the rate of change needed to cause a blur goes down considerably. When you are using a wide angle lens, it takes very large movements to cause a major change in the image since the image is so wide, however at focal lengths like 300mm (or 200mm on a crop sensor), any small motion is going to be a major change in the image due to the very small angle of view.
So, for any photo that has both a slowish shutter speed and a long focal length, you need some kind of stabilization to deal with camera shake. It can either be use of a monopod, tripod or some other form of stabilization or it can be optical image stabilization.
Monopods, and particularly tripods have the advantage that they not only address camera shake, but also other forms of motion, but they are also large and bulky and tripods are difficult to move when used properly.
Image stabilization on the other hand is much more limited in what it can deal with, but it is built in to the lens and can be with you all the time with no real impact on the usability or mobility of the camera. It's main limitation is that it can cause lag in movement because when you intend to move the camera, it will counteract it briefly. This can make it unsuitable for shooting anything moving quickly unless it has a special mode for that kind of situation.
It is really up to the preference of the photographer which they prefer. In cases where shutter speed is quick and/or focal length is not particularly long, there isn't much need for stabilization in general. When shooting from a stationary position where you can setup, a tripod is generally a better option. When photographing rapidly moving subjects, chances are good a tripod will be preferable. Other than that, it's a trade off of ease of use vs cost. There isn't a right answer, though personally I think it is worth adding up to 40% on the cost of the lens or $150, whichever is more, at least for general usefulness. Adjust that based on how often you expect to fit the use cases that image stabilization helps for.