I can't find any way to get to Akutan from Anchorage solely on PenAir. Seems like you have to go through Dutch Harbor, which is not allowed on my ticket.
I didn't say it too clearly, but Alaska Airlines also has the same restriction on redeeming PenAir award tickets to/from Dutch Harbor. They are referencing the non-stop flights from Anchorage, that must be bought through Alaska Airlines, and would count towards an Alaska Airlines award.
What I'm wondering is if you could redeem to Dutch Harbor via the actual PenAir flights that go through other villages. Though in your case I don't think it matters, as I believe you would need to make a stopover somewhere to get to/from Akutan as the non-Alaska flights don't connect.
The plan you listed sounds great though!