Problems? You bet.
Imagine if you will what it would be like if you were in the situation that an associate was in...
American citizen. In Cuba, through Mexico. Passport stolen in Cuba. Now what?
Go to Canadian Embassy, beg for them to contact U.S. State Department. New Passport arrives via official satchel from Quebec to Embassy (or Consulate) in Havanna. Then come home and face the music. Sure isn't a Cuban or Mexican jail, but a Federal Felony none the less. Lost their job, lost their home because of lost job, having hard time taking care of family because of working two jobs now.
I'm heading to Miami soon. My young son needs to learn of the world that's changing. I'll have a Cafe Cubano and a purro with the old men on Calle Ocho in Little Havanna. We will talk of the old Batista days and Kennedy. We will talk of the day when they can go back home, and I too can go, fish, drink Mojitos and smoke a good purro. Drink and smoke and laugh where Papa did.
Until then President Kennedy says no. A Castro is still in power and they remain believers in the cause while their people suffer. I for one will not defy the embargo. I will not risk criminal prosecution. I will not support a black market economy where the people suffer and the wealthy live above it all (Italian or not).
Plenty of old cars, mint drinks, decent cigars, and tarpon (a fish you can't even eat!) elsewhere.
CUBA LIBRE!
...my two cents.