Flying into Dutch Harbor is by small commercial airplane (Penninsula Airlines, or "Pen Air"), so it does not qualify as "bush pilot" flying. However, it has its own interesting quirks. Security is somewhat more relaxed in remote Alaskan locations like Nome, Barrow, and Dutch Harbor. For example, in transferring from Alaska Airlines to Pen Air, you have to leave the "security" area. However, you just present your boarding pass, and they don't screen you again, as they surely would in Spokane!
Luggage is often left behind in Anchorage, depending on the weight of the airplane. Passengers come first. Generally speaking, your bags are expected to arrive within 24-48 hours of your landing at "Dutch." George was lucky--he landed at 6:30 PM, and his bags came the next morning. This does mean that you have to do some extra planning--and the Unalaska residents just routinely figure this into their plans.
We'll see how lucky I am!