I also like it, and it's true, insinuating a random dude into a court system like that would be pretty difficult. It might be easier depending on the government type too. Like trying to get someone into a tribal council would probably be pretty tough, everyone knows everyone, but Aventura shouldn't be that hard since it's a republic. Look at all the ridiculous fucks who've gotten into US government over the years.
Not to mention, this isn't like the Rake is going up and applying for a seat at court. Most agents do their stuff through intermediaries, just like the old one acts through the agents. So in order to infiltrate court the Rake has to hire his own agents, bribe and blackmail people, forge documents to get his agents into various positions of power, and do all kinds of shit to both get influence in court and to avoid undue attention to himself.
Like in
this screenshot, the lost isn't actually sitting there at court looking spooky. He's got people whispering in various ears, leverage on voting members of court, etc.
Takes a long time.
My main worry is that since you have an absolute maximum of four agents before you've started really doing things to get more, and the fact that agents are your only real means of interacting with the world, means there'll be a lot of time spent clicking the next turn button and doing nothing else.