I agree with you: nothing works. That's the problem.
Clearly, though, there is historic change about to happen in Cuba. Will it be in a few months? Will it be in a year or the next couple of years? One doesn't know. One has been hearing for quite a while that Fidel Castro is ill and aging and about to depart from the scene, but it is actually happening.
Canada is limited in what it can do right now, given the context on the ground in Cuba. I do agree that just out of principle, it should assert its democratic principles more forcefully and explain to the Cubans in a respectful way that there are other models out there, including ours here in Canada, which are not the American model, but democratic, capitalist systems that are also socially progressive. That is what the Cubans actually aspire to; however, here it's economically viable.
Definitely, one should assert oneself at this stage, but one should be very realistic that it's limited in terms of the kind of change that one could influence right now while Fidel Castro is at the helm.
We should be doing a lot of preparatory work at this stage to be planning for the big change that is about to happen and try to influence that change in a positive direction. A key recommendation I would make to do that would be to try to come up with some sort of concerted strategy with the international community. One idea would be to put together a golden carrot to influence potential reformers on the island to take the steps we would like them to take.