Puerto Rico "develops" in a way similar to that of the Dominican Republic or worse, like Haiti. One butterfly I'd like to see people comment on is- does the USA still buy the Danish West Indies (US Virgin Islands) from Denmark in 1917? The US Virgin Islands become harder to defend without the larger landmass of PR next door to provide more room military bases. Cuba as a US territory probably goes similar in development as the Philippines, the US holds it against guerrilla insurgents but muckrackers in the news draw parallels to what the Spanish did and "why are we in Cuba?" becomes an anthem for the political party not in power. Either Cuba gets independence shortly after WWI during the inter-war period or there becomes a big decision for the US Congress after WWII when Cuba is put on the list of non-self-governing territories (as the Philippines, Alaska, and Hawai'i really were in OTL); Hawaii and Alaska were a lot easier to assimilate than Cuba will be, plus there was a balance of political parties allowing Alaska which was assumed Democrat, Hawaii Republican; oh how times changed! No balance to Cuba, can't really split a Hispanic nation in to two or more US states (at least four Hispanic senators? Not in the 1940s or 50s would that be considered). Cuba goes independent. American interference and economic control the same as OTL, still a communist revolution and the ATL and OTL pretty much merge with the exception of a poor and independent Puerto Rico the US marines go to once a decade to clean house of some former pro-Western dictator who got too much attention about his purges.