I don't think so. Unless teleportation gets perfected in the next 10 years or so I feel like instead of expanding MLB officially to places like Cuba and EU they will instead just make 3 more leagues in general perhaps EU, Asia and Central America.
The MLB season would be left mostly alone just the world series would change. It would be the MLB series instead and then the champ from MLB would face off against one of the other leagues while the other two would face. And then the winners of those would face in the final world series to make the name finally fitting.
The problem with that though is there isn't as much money for the other leagues, so either MLB would be overly stacked with talent and it wouldn't even be a good final match up, or the talent stays in their areas and MLB in general has less superstars to draw attention which could hurt ratings.
logistics aside it would be great to see baseball become more of a world wide thing.
eh i don't think transportation would be a big hurdle. Havana is only an hour flight from Miami. 2hrs from Atlanta. About 5 hours from LA. (according to travelmath.com)
Just make a new Division. Atlanta, Miami, Tampa Bay, Havana and Washington (or hey, put a team in Puerto Rico) (edit, looks like PR is the same flight time as DC)
DC to Havana 2hrs 46min
Atlanta to Havana 1hr 59min
Tampa Bay to Havana 39min
Miami to Havana 57min
With the way the schedules are set up. Most of the games are played within the divisions now so it wouldn't be that big of an issue for the other team. Just need to schedule it so they play all of those teams at one time like teams do with the east and west coast teams.
(i mean if the braves can play in the NL West for all of those years then you can put a team anywhere).