Coming from a different situation -- all systems are repressive to some degree or other, but some are more repressive than others, or even than they need to be. Still, Brad de Long's proposals are pie-in-sky stuff that invites Gandhi's retort about western civilisation.
Re this business of US financing: I have no idea what the current sentiment of Cubans are, but would not revelation of US funding for a political party result in that party being reviled? In, say, Malaysia, the ruling party trots out such charges of foreign funding seeking to undermine Malaysia's independence against groups -- NGO's, e.g. -- it doesn't like. It does this because it figures it can rely on majority sentiment to reject something like that; it even employs Australian consultancies to produce a report showing how NGOs with foreign funding follow their funder's agenda, throwing the NGOs on the defensive, at least for a while. Because of this, political parties stay away from foreign funding.
Then there are a panoply of laws requiring annual licensing for periodical publication, for radio and tv, harsh terms for 'false news', etc. All of which helps them keep others out of print and off the air. It can hold back foreign magazines for 'vetting', for weeks. It bans books, including recently a bible in one of the indigenous languages. All shows, theatre included, have to get a permit, plays have their scripts vetted. All assemblies need a police permit, and any assembly of more than five without a permit is an unlawful assembly. Any person convicted of an offence carrying a fine of more than the equivalent of US500 or a jail term of 2 or more years is dis-barred from standing for Parliament for a period of 5 years.
As well, a long established law of preventive detention. Currently, there are half a dozen activists from an opposition political party who just finished their two years in preventive/pre-emptive detention under the country's internal security laws -- the government now takes pleasure in noting that the US has adopted its practices! -- and have had the term renewed: it's renewable every two years for as long as it takes, and in the past there have been people spending up to 18 years in such detention. There are loads more of others under such detention for being Islamic extremists or deviants (and the US wants access to them); in the past, it used to be for 'communist subversion' or 'anti-national activity'.
But really, at the end of the day, it has never lost power in over forty years because (i) the majority of people are not touched by these laws for venting their sentiments in coffee shops, (ii) it delivers enough of the goods, (iii) it can count on the desire for stability trumping the desire for change, especially when it can point to so many other countries in disorder, (iv) it has the advantage of incumbency and the use of state instruments to buttress it, (v) it has built up a solid constituency of support and can gerry-mander constituency boundaries and composition to its advantage, and so on. In other words, it actually doesn't need to be as repressive as it is, although that doesn't hurt, and it keeps the repression within the 'comfort zone' of a majority.
The point of all this being -- even if Cuba were to adopt some or all of these practices, no mass railroading, quick trials and long sentences, it would still come under much greater pressure than Malaysia. Malaysia might merit a line in the State Dept's annual report, and a report now and again from HRW, but otherwise nothing untoward.
But really, Cuba should adopt some such combination of instruments.
kjk