"Even by generous definitions, genuine, fully functioning democracy and rule of law are rare in Latin American history and culture"
Your friend is indeed an alarmist.
If I personally had the power the power, I could present to Congress an organized State of Puerto Rico tomorrow, accrding to the Tennesse Plan. It jus so happens that the very powerful lobby of the oligarchs that profit from our colonial condition do not allow it to happen. Mainly through the spreading of unfortunate stereotypes such as the one you project here.
I'll tell, ya. I read with amusement about the opposition to new states throughout U.S. history. They all follow the same script. The day before yesterday it was the railroads, yesterday the United Fruit Company and today it's the multinational manufacturers.
I must have missed the part of your post where you listed the stable, long-existing Latin American democracies with a solid tradition of freedom and rule of law. Would it be unfairly stereotypic of me to offer to list Latin America's wars, dictatorships, and coups?
Independence, then statehood by free choice and petition is the best formula for Puerto Rico. That is how Texas was admitted, and surely Puerto Ricans ought to appreciate the opportunity to have valid cause for the same swagger as Texans.