I don't think that a relationship with Cuba is very good until they begin to give more rights to their citizens. I have this stance against any regime.
Despite what some people think, the money does not trickle down to the poor in any shape or form. Not even for education or health. It only goes to the dictators. If you don't believe me, take a look at the hospital the average Cuban goes to and just imagine if Castro would be seen dead in a place like that. I have family that sent pictures when their child was born and the walls are bare cinder-blocks. It is extremely sad what they go through there, so much so they are willing to risk their lives to get somewhere else.
As for what just happened this week between the US and Cuba, I do not think it is very significant, unless you want cigars. Travel for Americans is not going to change. It will be too much of a hassle, especially when so many other options in the Caribbean exist, such as the Dominican Republic.
As for raising the limit on how much money Americans can send there, that is a token law since people sent whatever they wanted to anyway. No one was keeping count.