The US will treat Cuba like a clearance sale if it has the chance to. Everything must go; especially if it's deemed too 'socialist.'
Cuba will either be under America's heel as it is now under a continued Castro regime, or at it's teat like it was under Batista.
Why would they when they don't with Canada which has over its history had some pretty socialistic elements. While not much state ownership today, we did in 70s have a lot more including a state owned oil company (Petro-Canada, which is now privatized), government run health care which unlike most European countries actually bans private competition for basic care (or at least tries to). Canada historically had very restrictive foreign ownership laws and even had a foreign investment review board that frequently blocked foreign investments up until early 80s. Yet US never intervened. They may have not liked our more left wing approach, but we were able to do so. Thus I think as long as no more socialistic than Canada has been at its left wing peak they should be fine. And right now, millennials are very left wing in Canada so good chance you see us zoom quite a bit left in next 20 years. If US intervenes in Cuba but not Canada would look hypocritical.
Off course US isn't always consistent in foreign policy thus maybe won't let Cuba do some things that allow in Canada, but at least I think as people are more aware, American public won't react too kindly to a double standard.
We had exchange controls until 1979.