Lumping the Virgin Islands into a single polity with Guam, Samoa, and the Marianas seems like a good way to make lots of people unhappy and please no one.
Why?
It’s better than what the 4 have now.
What makes you think the people of the Virgin Islands want their congresspeople being selected by people who live on the literal other side of the planet from them? Or that one person could effectively serve both those vastly different constituencies?
Because not every small island should get their own Representative & Senators & Electoral votes. Combined the four organized territories have a population only about 2/3 of Wyoming so although USVI might complain, the rest of the country would agree that the OTs should not be four political bodies. And if the USVI wants to complain that they now have some representation and voting rights, remind them that you don’t always get what you want, but just sometimes you get what you need.
“Congratulations, your congressmen and Senators live 10,000 miles away from you and will never visit you or have any town halls for you or represent you in any meaningful way because your population is statistically too small to have any say in who gets elected, now stop complaining and just be grateful we gave you anything at all”?
That’s gonna be a hard sell.
Luckily, under my plan it is a constitutional amendment so they won’t get to vote on it.
So do the Virgin Islanders get any say in this plan, or are you just annexing them into Greater Micronesia whether they like it or not?
First of all the reality, USVI has less than 1/5 the population of Wyoming so there is absolutely no way the other political bodies will let them be a separate body with 1 Rep, 2 Senators and 3 EVs. That will not happen.
And I deny your premise that most USVIers would object to any plan that would give them representation and EVs. If there are significant numbers that will be upset by that given the alternative is nothing then we should change their name to Island of Karens and they are more than welcome to speak to my manager.
I eagerly look forward to the ads you’ll be running to persuade Virgin Islanders to vote for this plan. May I suggest “Take it or leave it, assholes!” as the tagline?
Incidentally, the last time seeking statehood was put up for a vote in the USVI, 87% of voters voted against it.
Great strawman! This is not about statehood - merely Americans being represented in Congress and being able to vote for President. And they care so much on the issue that less than 30% even voted. 
And you still have yet to explain why the USVIers would prefer to not have representation and EVs and would prefer to have no rights in that arena.
Have you considered that asking them what they want might be a better way to go about things than imposong a system upon themcwith or without their approval, especially when the idea is to undo a legacy of colonialism?
No!
Because this is about all Americans having the right of representation and voting. I don’t give any cares if 80% or whatever it really is don’t want those rights because the other 20% or whatever deserve them. To deny them their rights is the Tyranny of the Majority and here is the ultimate kicker - if you choose not to exercise your rights as an American you don’t have to. If a USVIer is so angry that they have rights where none existed before, then the solution is to not contact your Congresspeople on any issue and don’t vote for President.
Let me ask you this. 80% (again I deny that number represents how many would object to my plan but let’s go with it) of the people in your state vote to not elect representatives, senators and the president. Because of this you lose those rights as an American. Are you OK with that because the majority has spoken? I believe in the Southern states there was a time when the majority thought Black Americans shouldn’t vote. I assume you’re OK with that since that is what “they” (the state) wanted.
Rights are not subject to the whim of the people nor should they. Where do you come down on the Texas abortion law? If you believe abortion is a right, you still can’t complain about what Texas did because that what they want.
If we’re doing impossible fantasy constitutional amendments to provide for territorial representation now, my solution would give the small territories their own whole members, but they would have fractional votes. Instead of dividing one person between four disparate territories, you could have one vote divided between four representatives.
Just increase the size of Congress, along with the EC, and make each territory a state (if they want it). So the smallest territory gets 1 House Rep, and their population size becomes the ‘standard’ amount for 1 House Rep. Yes, they’ll each get two Senators – and now Wyoming will know how California feels.
As long as we’re offering hypothetical Constitutional amendments.
This is totally unworkable. It would give us a House of Representatives with 6,000 seats. Even the fake Chinese rubberstamp legislature only has 3,000!
Then in my hypothetical I’m building, I will take out “manner thereof” in how the Feds can control congressional elections so that states can use proportional representation instead of districts if they want.
6000 people isn’t that many. There are high school basketball stadiums that can seat 6000 people.
I’m not talking about the size of the building. There is no legislative purpose for that many separate people to be involved.
Giving fair representation to every American seems like a good reason to me. Not sure if that’s a legislative reason, but it’s still a good reason.
Define fair. Because usually that means everyone is equally represented so each rep would have to represent the same number of people. That also means the representation factor should change continually as population changes and as that will likely at some point in time be a prime number the only “fair” system is where everyone has their own individual Representative (or 1 Representative only).