I don't think the Philippines were ever a serious case for statehood. It had only a minority position among Filipinos, and even less among Americans. The US only reluctantly decided to claim Philippines as a colony, and done more to prevent a European power or the Japanese from doing it than anything else.
For Cuba, the longer Cuba remains outside US control, the harder it will be to make Cuba a state. The most likely departure that sees Cuba becoming a state is probably before the Spanish-American War.
President Polk instructed the US minister to Spain, Romulus Mitchell Saunders, to purchase Cuba for the very high price of $100 million (the price was high presumably because Cuba had a very profitable plantation economy) in 1848. Spain refused because of a combination of pride (it was their last colony and didn't want to lose it) and finances (since the colony was very profitable). If for some reason Spain decided to sell Cuba then, it would be the best time for Cuba to become a state. There was still support in Congress at the time to do so, but soon afterwards slavery politics would make it impossible. The US could have coopted the native elites so that their desires would not become for an independent Cuba, but liberty and self-government as a US state. Once a true independence movement began and fighting occurred, it would be much harder for that to happen.