Cuba really doesn't have much of a choice, they have to trade with "friendly" nations of which America refuses to be.
Fun fact, when we (Canadians) go to Cuba they typically won't stamp our passports because they know it causes us issues when trying to enter the US.
(Or, at least, offer subsidies to their government if they stop supporting Russian and Chinese spies with their numbers stations et al.)
Mind you, I am not saying there is an existential possibility of a better policy, but the calculus would be nowhere as trivial as this.
I mean, certainly, but it's like having a club on your car's steering wheel: it's not about creating perfect protection, it's about ensuring your car isn't the softest target for theft in the parking lot.
If Cuba had fewer reasons to talk to Russia and China, then Russia and China would have fewer reasons to talk to Cuba in particular, vs. other Caribbean and Central American nations. Which would, potentially, spread their resources thinner and decrease covert-ops ROI, as they'd be having to engage with several nations who only weakly want them there, instead of one nation that desperately wants them there.
(And yes, I do realize that these powers do already engage with other nations in the area, e.g. Nicaragua. But not in the same way / not for the same reasons.)
Also, if you want to talk about countries that the US actually gives "special attention" to, I'd more compare/contrast to the relationship between the US and Panama.
Cuba would have do what those other ex-USSR satellites did and discard communism and authoritarianism in favor of democracy. Then, yes, seeing themselves as a sovereign state would be a good thing.
But I'm not sure if such an alignment could be created between the US and Cuba while Cuba remains a communist authoritarian hereditary dictatorship, since there's no shared enemy nearby and no strong shared economic incentive. Seems like the only real alignment would be Cuba becoming a democracy.
I think the West gains a lot more by having generally available VPN access in adversary states than it loses from their ability to purchase technical services that they still will have difficulty getting access to currency to pay for and they still will have difficulty actually shipping anything to NK.
Yes? Making it easier for North Korean citizens, or even just leadership, to communicate privately with each other and with people outside makes it easier for them to negotiate or even defect, and would help de-escalation efforts.
> What might the reasons be on the "no" side?
I guess one could argue that the North Korean government doesn't have access to secure VPN systems for government use (pretty implausible IMO) and that increasing their costs is inherently worth it? Realistically most of the opposition would come from those who benefit from the status quo (e.g. arms suppliers) and don't want to see that de-escalation, and I guess the extremely risk averse who would rather keep kicking the can indefinitely and hoping the blowup doesn't come until after they're dead, than risk actually trying to help North Korea's people.