It might help people to see some local journalistic coverage of Cuban elections. Seeing the kinds of things Cubans say publicly about and during the elections can give people a more intuitive understanding of what Cuban democracy is actually like for the people participating in it, as well as start to reveal the outlines of the overton window there.
Journalism is my preferred medium for understanding the political landscape of other countries; for an example I like to watch friendlyjordies on youtube for a peek into Australian politics. I’m not sure if it would be very easy to find English translated Cuban sources though.
They’ll just make legal carveouts for government and commercial use, and go after consumer-facing VPN providers that refuse to comply. For VPN providers based outside the US, they could delist their websites from DNS or block their IPs. They can’t stop someone who’s determined from finding a way, of course, but just a few simple barriers prevents most people from putting in the effort.