For a fun and light read I’d start with Wikipedia entry on the attempts on the life of Fidel Castro.
For chronological read I’d start with Iran then Latin America, Wikipedia as well. Don’t skip the chapter where they associated themselves with drug lords that sent drugs to US as a way to finance anti communist operations in Central America. I think that was Nicaragua.
The software I use doesn’t get significant updates often. Kennel, vi, grep, find? They’ve been around for decades.
I’m genuinely curious what kind of things people can’t do because of lag on package updates.