First, perhaps the Democrats being able to win Florida in a presidential election gives them comfort they can pull the new policy off without alienating the
Two, Canada's had a rational Cuban policy for a long time and they seem to be doing fine with it.
Three, the way to just finish the job of getting the mob back to its rightful place running Habana casinos? Airdrop the equivalent of hundreds of malls' contents on the island, and sell the exclusive marketing rights in each product category to whichever company wants to get the initial foothold in the market.
Pop, computers, clothes, whatever. Get some retail sales going.
Think of it as a Caribbean stimulus package.