I can freely admit that I don't know much about Cuba's isolationist history nor do I fully understand the Cold War mindset that had a part in shaping it, but I've got a few thoughts on the matter.
Rapprochement is the term that I guess would be used to describe this, and I have to wonder if it's really been used since the Nixon days. I know as far back as 2009 Obama wanted to have a "new beginning" with Cuba, and I suppose that relaxing travel between countries was an opening act. I think America, as well as other countries, have/could stand to learn that playing the role of enemy doesn't work in their favor or serve to advance democracy (whatever your definition may be) in Cuba, but involvement with other countries besides us haven't had much difference either, and that can be attributed to Cuba's own internal workings, not outside influences.
As far as I know, Cuba is under no real obligation to change or dismantle its style of governing but it does now have to deal with justifying it to another (sometimes overbearing) audience. Not doing so endangers it building any kind of relationship with us. However, doesn't doing so also endanger their current regime? Agreements with us allow them to accept our visitors and our money, at whatever point the embargo(es) are lifted, allow them to enter trade deals with us, but all that may/will most likely depend on more communication and reforms than their government has allowed so far. If they were to renege on the opportunities offered now, they may instigate anger not only from us, but possibly even from their own citizens.
In short, while I'm in favor of opening relations with a country that's long been closed off to us, I guess I can also realize that this new course of action could prove to be a big gamble on both governments' parts, with one winning and one possibly losing. I don't like to think that that could be what ends up happening, but maybe it's not as difficult for me to be more straightforward because, as I mentioned before, I didn't grow up with us being newly afraid of Cuba, I've always known them to be just....alien.
:dunno: