VidaNaPraia

Havana has cobblestone streets and bad paving, as do many other places. Might be hard to use a stroller of any kind.
The heat and humidity in Cuba can be quite intense, even in May. Your baby might be uncomfortable and fussy if unused to this.
It also means a baby backpack carrier or front snugli might be uncomfortable for a parent.
Also, baby products (diapers, rash cream, milk/formula and food, etc) are most often not easy to find, so bring everything you might need for the baby.

Note: Trump has not reversed anything. ONE category of independent travel has been removed. That's it. The damper is in uninformed travelers' heads only.