While I would never make a public blanket statement to ignore OFAC regulations as they relate to Cuba travel because they have not been enforced for at least 15 years, I do think that is a risk mitigation factor worthy of consideration.
Many would be surprised to realize that the actual Cuban travel regulations including the 12 exemptions have changed only insignificantly for at least 10 years (my era) I do believe they are much older than that. Realistically the only change has been in the traveler’s required documentation.
Until some 3-4 years ago, about half of the exemptions qualified for a general license (i.e. “self certification”) These were for family visits, government employees on official business, and others. The other half, which included all of those relating to casual travel (i.e. “person to person” & “support for the Cuban people”) required a specific license. A specific license was an actual piece of paper obtained after OFAC reviewed your specific schedule and all activities and approved such. I once traveled with one of those in 2009. The requirements to obtain OFAC approval were rigid. I was also once denied one of these specific licenses.
About 3 years ago, Obama changed the requirement to obtain the written specific license and made all travel permissible under a general license. This is the infamous “self certification”. None of the actual requirements changed, travelers were simply no longer required to obtain pre-approval. This was generally but incorrectly interpreted to mean “Cuba is open” or “no more stringent rules”. Again, the regulations and legalities never changed.
Back when a specific license (i.e. written pre-approval) there was clear detailed documentation with examples published by OFAC as to what would meet the requirements for approval and what would not. Additionally, everyone was aware of such from informal public information about licensed granted and licenses denied. BTW, “full time schedule” meant there was no time for anything else.
But when the need for specific licenses went away, all the official OFAC guidance just disappeared. They all simply became dead web links. No indication if what once was allowable had changed, been rescinded, or remained in effect. Just silence from OFAC. My personal belief is that Obama made everything so undefined and convoluted that no regulations could ever be enforced. Trump never tighten this as he never cared or had resources to do so. All Trump wanted was some lip service to get Senator Marco Rubio off his back.
Looking at the regulations which have remained unchanged for many years and OFAC current limited published interpretations, they appear simple. But if one goes back 3-4 years and see what was once published but then unpublished with no notification that OFAC posture had changed, everything becomes convoluted and contradictory.
That is the basis of my opinion why the OFAC regulations cannot be interpreted or enforced. But I have no problems with those who lacking information create some mental scenario that they are perfectly legitimate. Nor do I worry about them because of non enforcement.
BTW, it would be great to start a list of popular internet myths about Cuban travel from the US. Things like “now you can fly direct to Cuba from the US” when in reality that has existed since 1990.