In reality, Cuba NEVER really had much of an infrastructure. When I was there in the mid to late 1950s, most of the roads outside Havana were dirt trails that were barely passable in the dry season. When it rained, they became a quagmire and the only way to reach some of the remote towns was via boat or muleback.
Most of this did not change when the Russians supported Fidel. Their support amounted to next to nothing, other than money they funneled into the Castro regime and the few jobs created outside the military to support the missile bases. When the missiles left, so did the money.
I was in Havana before Castro, it was a wide open town, gambling, prostitution, etc... - just like Chicago back in the 30s. The only thing missing was Al Capone.
(He may have been lurking in the shadows, though.)
The biggest employer in Cuba during the 1950s was the US Navy at Guantanamo Bay Naval Center. Every morning, a huge line of folks from nearby Havana and some of the surrounding towns entered the base via the main gate. Most have menial jobs, serving food, cleaning, gardening, maintenance of sorts, but they all made more money in a single week back then than they do in six months today.
Back then, many Cubans that worked on the base, also had jobs in Havana restaurants, casinos, grocery stores, and quaint shops around town, many of which I visited when I was there. It was neat to see all the handmade, wooden carvings and statuary, one of which was made of black ebony that I purchased and still have in my livingroom today.
I never saw the mystique with Cuban cigars, but I never really enjoyed cigars to begin with. I have a friend that participated in the Mureal Boat Lift, damned near lost 75-foot charter fishing boat to the Cuban government, spent a week in a Cuban prison just for being there. He got out with the boat and the shirt on his back - lucky to be alive I guess. He said he never witnessed such cruelty to others and abject poverty that existed at that time.
I really have no desire to return to Cuba, even if it turns into a vacation resort. There are lots and lots of fascinating islands in that part of the world, islands that we can explore and learn about the local cuisine and culture. I guess some folks feel that they must test the forbidden fruit by visiting Cuba, but I'm not among them.