It would really be hit or miss. If you went for a week in the late fall or winter, you'd have a good chance of getting surfable waves. Keep an eye on that NDB cam and you'll get a good idea of how often it works. But if it's a snowy winter, you'd have to walk in to the break, which would be maybe a half mile. Also, if it's a snowy winter, you may have to walk to Summer Bay. The road is always maintained to the dump, but beyond that slides may close the road.

The weather is so amazingly variable it's really hard to predict anything.

I never saw them myself, but I heard that some dudes from a surfing magazine come up every year and surf in Nikolski. That's a neighboring island, and the reason it's more consistent is that you can access the pacific. (All the Dutch Harbor spots are Bering Sea swells). Unless you are super rich, you'd have to camp in Nikolski. They do have one high end hunting lodge. And of course, flights to Nikolski are frequently canceled.

There are two other options that I never got a chance to do, and they would involve being dropped off at the either of the ranches. One is on the east end of Nikolski - and you can contact them to arrange a stay. It has access to the Pacific. The other would be to get dropped off at the sheep ranch at the south end of Unalaska Island and hike down to the Pacific. Either way would either involve flying on the Goose or finding a fishing boat that would be willing to drop you off.

You should also be aware that DUT is one of Alaska Air's most expensive flights. It's excellent value to use miles to get there.