Just make Puerto Rico and the District of Columbia states already. They're pretty much states by now except not-in-name. I don't care about the politics behind it and whether that means gains for Democrats, I just think they both deserve representation by this point in the House and Senate.
What they should do is have DC become a state, PR with the Virgin Islands become a state, and the Northern Marianas, Guam and American Samoa combine to form one state.
I agree 100% with this, the only issue is that population of Pacifica (my persona preference for a name) would probably be too small for a state with just American Samoa, Guam, and the Northern Mariana Islands. Now you would probably get a big enough population if you included Associated states, the countries that are technically independent but relay in the United States for a log (defense, funding, currency, government services, etc). If you add these locations (Federated States of Micronesia, Marshal Islands, and Palau) you get a population of 469,305.