Yes, it's a tricky issue, but I believe that the evidence is clear, if painful due to history.

First, as a general principle, we ought not to have any sort of second-class citizen. Those who live under Uncle Sam's umbrella, even under the beach umbrella at the seaside house, should enjoy His protection and benefits.

American Samoa is the best example of a practice I find unconscionable: We allow and encourage American Samoans to serve in the armed forces. And, unlike in the films, service doesn't even guarantee citizenship. While I understand that the economic opportunities in mainland USA are lucrative for natives of Guam, FSM, or American Samoa, I believe that the military is predatory in its recruiting and unfairly targets unwitting young islanders.

American Samoans are akin to Puerto Ricans in that their representation in Washington, DC is limited to a non-voting delegation. The past few years have shown the futility of hoping for non-voting delegations to shift legislators' opinions; we need for those delegates to have votes in order to effect legislative change.

A final note about American Samoa is that, as I understand it, there is a movement for independence from both Western Samoa and the USA. I don't think that they have to be part of the USA if they don't want to belong! I merely don't want them to be disenfranchised.

With that said, let's remember the history of Hawaii. It is a complicated and gnarled story, with monarchs, rebellions, colonialism, racism, banana republic, and finally statehood. It's only with statehood that Hawaii gained a strong tradition of spending public funds on preserving and understanding the history of the Hawaiians, and shifted the focus of government away from constant exploitation and segregation. It's not perfect, but I can't help but want the same guarantees and improvements for the people of Puerto Rico.

Finally, yes, let's consider the House. Let's imagine that we implement the Wyoming rule: The House is reapportioned so that each Representative is worth the least populous state. (When the rule was named, guess who was least populated?) We'll set this at 55K for today. NMI and American Samoa get one, US Virgin Islands get 2, Guam gets 3, Wyoming gets 10. Alaska gets 13. California gets, uh, 719. Nope. Fun, but nope. A legislative body of over 5K people is not practical.

Edit: Even better, what about Puerto Rico, population ~3M? They should have at least as much representation as dozens of other states with less population, shouldn't they? [2] I'm redoing the numbers below including Puerto Rico and DC.

Let's try again. When Arizona and New Mexico first came into the Union, the law [0] allowed for new Representatives to be chosen, and for the size of the House to grow by one Representative per admitted state. Additionally, the law held the door open for increasing the size of the House incrementally after every census. However, by the time that Alaska and Hawaii were admitted, legislative gridlock had ruined this plan, and the House's size had become fixed by a different law [1].

The upshot of this history lesson is that, had we given one Representative to each new state after 1911, then we're talking about 22/(444+112) = 3.9%. Scary! But, had we not just continued to add Reps, but also diluted their strength by half (keeping in mind that Rep strength has tripled over the past century!) then we're still talking about 22/(888+112) = 2%. That sounds like a reasonable compromise, given that they currently have 0% and that we're talking about some 1-2% of the population.

[0] https://en.wikipedia.org/wiki/Apportionment_Act_of_1911

[1] https://en.wikipedia.org/wiki/Reapportionment_Act_of_1929

[2] https://en.wikipedia.org/wiki/List_of_states_and_territories...