(1) The differences in their stated positions are absolutely miniscule.
Both state that they think the embargo should be in place unless and until there are possibilities of democratic change in a post-Fidel Cuba. Both say that the 2004 policy of restricting remittances from Cuban-American families should be overturned. Both have indicated, through a 2005 vote, that they think the current policy of only allowing Cuban-Americans to travel to Cuba 14 days every three years should be eased for humanitarian exceptions.
The only stated difference in their positions is that Obama has added that he thinks the restriction on travel by Cuban-Americans (not by anyone else) should be completed lifted. So whereas Hillary has voted to allow Cuban Americans (only) to travel to Cuba whenever necessary in circumstances (plus the already alloted 14 days per three years), Obama said that, when he becomes president, he would additionally allow Cuban-Americans (only) to travel to Cuba as they please.
(I don't believe Hillary explicitly indicated she wouldn't support that, just that she didn't entertain "broad changes" to travel restrictions at this time; "broad changes" could be interpreted to mean either those that Obama suggests or other broader changes such as allowing any American to travel to Cuba.)
In other words, pretty narrow differences!
(2) Even these extremely narrow differences in state position would likely never amount to any actual differences in policy.
Obama's editorial in the Miami Herald did not discuss trying to make these changes now; he merely said he would implement them if and when elected president, in other words 17 months from now. Within 17 months, a heck of a lot could happen in Cuba, such as Fidel Castro dying. I expect that by the time a Democratic president assumed office and got to this issue, there might be a lot more to discuss than these very narrow changes.
(3) What then is the real substance of the difference?
If there position on these matters is so extremely narrow, why the big to do? Well, it's simply this. Hillary has about a 60+% chance (according to oddsmakers, and certainly in her own mind) of winning the nomination. Therefore, she's campaigning with the general election in mind. She's not going to seize on essentially small and symbolic matters that might cause her difficulty in the general election. (As people have pointed out, Cuban opinion is split on this issue in Florida, but certainly from the point of view of the general election it seems doubtful that emphasizing an easing of restrictions will help the Democratic nominee.) With a very strong lead in the polls, she's right to play things a bit cautious and avoid giving her Republican opponents ammunition.
Obama, on the other hand, has about a 20% chance (again, according to oddsmakers) of winning the nomination. He thus has to run with the primaries first and foremost in mind. He needs to create some distance between himself and Hillary now, even if there's a small risk that could cost him in the general election. Therefore it makes all the sense in the world for him to be a bit bolder in emphasizing steps he would take.
(4) Summary
There positions are extremely close. Both support the continuation of the embargo for now, both call for an end to bans on remittances, neither call for an end to travel restrictions on any Americans other than Cuban-Americans, and both support an easing of restrictions on travel by Cuban Americans (Hillary for humanitarian reasons, Obama for any reasons).
The only real difference is the way they are spinning this issue. Obama is seeking to emphasize the boldness of what is really a mild incremental step, in order to create some momentum for his primary campaign. That is right for him to do, given her current position.
Hillary, on the other hand, is trying to downplay the mild incremental steps she supports, in order not to take any risks for the general election campaign. That is right for her to do, given her current position.
(5) One Final Point
Isn't openness always better than not being open? Well, not necessarily. As other people on DailyKos have pointed out, it would be political suicide to state one's open feelings on some issues, such as support for gay marriage. The principal of openness has to be combined with the goal of winning elections. I will let others debate back and forth how positions and emphases on this issue could affect the electoral calculus in Florida (probably, given the mild stands being discussed, not much either way in either the primary or general election--though, as we've seen in Florida, even small differences can make a difference!) Again, I think that Obama is right, from his perspective of shaking things up in the primary, and Clinton is right in trying to neutralize opposition in the general election. And as far as what policy will actually be implemented vis-a-vis Cuba, well, that will obviously depend on the situation on the ground in January 2009. (But I expect that both would be open to serious change in discussion with the Cuban government. Even under the Bill Clinton administration, less restrictive policies were in place than those now.)
So, flame away!
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