To how many places how many times a day?

You seem to be forgetting one of Southwest's rules of adding airports (besides quick turns): They don't add airports unless they can justify at less 10 flights a day from that airport, spread over several destinations, typically a mix of the closest ones outside of 3 hour driving time and one or more of their semi-hubs (Baltimore, Chicago, Phoenix, Las Vegas, Orlando, etc).

So it's unrealistic to just look at whether Southwest could fly to SOMEWHERE from Hawaii or Alaska, but whether they could fly OFTEN ENOUGH to ENOUGH DIFFERENT destinations from there to make starting service there (on their point-to-point model) practical.