Premise
The world in which this takes place is a realistic world set in the year 2040 where technology has advanced beyond where we are currently, and the government has grown more corrupt. Most of the working class has just accepted the fact that the government is watching over them, and is okay with it, sacrificing their own freedom for increased security. There are a few people in the city that don't agree with it though. All but one stays silent and won't do anything about it in fear of retribution. The government isn't a democracy as we have today, but is a complex bureaucratic dictatorship in which the government gained the approval of the people through tricking them into thinking that this is what's best for the society in an environment of social complacency.
Protagonist
The protagonist's entire bloodline on his father’s side has had some history of disrupting technologies. He also was taught from a young age about hacking and taking apart computers and putting them back together. He doesn't know what he wants to do after he takes down the government, just that his goal is to take it down before the government takes control of the entire world and enslaves the world’s populations under the guise of safety.
Government
The government has been planning to do what they have done currently for many years, since the year 2025. They took advantage of the fact that most of the population, while okay with the fact that there was crime, ultimately wanted no crime. This was their first foothold into getting the entire country on board, they then started implementing the surveillance into major cities, where crime was abundant, so that they could get other cities on board with data that showed that the way they do things actually lowers crime, not just theoretically. After about 10 years of pushing to new cities, the last of the small cities gave in and accepted the government's plan. With this newfound access to everyone's data, they started to abuse their power behind the scenes. Getting people fired by leaking info anonymously to employers, selling private data to big businesses outside of the country to better target products to people living in it. Some people started to catch onto the government as they did this, and like any other corrupt government, they put the loudmouths down to make a point. Pretty soon everyone who opposed the idea quieted down and went into hiding as to not paint a target on their back.
EDIT The government is a single country, that has ambition to become a world order.
Plans
One plan is probably the most common and straight forward, which would be to get into the government’s network and start turning the computers "against" themselves. When I say "against", I mean getting them off the government network and setting up a secondary secure network just to get them out of the government’s control. Another plan is to sabotage some of the network stations in the city to get the government to come out to the site, then using force they gain their badges and clothing, and then infiltrates the site, taking out the dictator and putting an end to everything. If everything goes south and they needs a last ditch effort to take down everything, they have developed a worm that can bypass any form of firewall or security and start uploading files to cause a self-destruct of all the files relating to the program, including any backups.
Question
Given the size of the government, and the level of integration into society, would any of the plans listed have any chance of success?