To this end, you can only recruit people up to what you can afford using your stable income. Robbing houses may give you disposable cash on hand for one time purchases, but ongoing expenses, such as rental costs for new safehouses, and salary for new recruits, will need to paid from stable income. At the start of the game, that's your trust fund, but you may feel the need to secure additional sources of income.
I humbly suggest not doing this. It goes against the very grain of the game that you're creating.
Limiting someone to what they can afford is
Socialist and Un-American. Rich people are always trying to leverage their future for an advantage today. Maybe the player has a surefire plan that will net them untold riches in the future by picking up more recruits than they can pay for today. Why not let them try it?
After all, what's the worst that happens? Your star recruits bail out - Their employees, not brothers-in-arms. You get new ones when you get the finances straightened out. Maybe even hire them back if they don't find work in the interim.
It seems to me that the player's character is the sort to think their smarter than everyone else, so they should be able to take such risks and face the consequences.
...and if the player gets raided just after their security guards walk out for insufficient pay, then maybe they'll learn something if they survive.
As for your doubts:
I was also worried about the state of American politics, until I went to an Art Museum and was reminded of our history.
1804: Aaron Burr and Hamilton duel. That's right, two duly-elected officials pointed guns at each other and tried to kill one another.
There were subsequent fights between elected officials in the Assembly and Senate leading up the American Civil War.
1861: The American Civil War starts. Our country actually splits in half along party lines into open warfare.
Early 1900s: Communists form groups dedicated to the overthrow of the capitalist world.
Domestic bombings and riots during the Vietnam war, The Black Day in July.
Honestly, things are pretty peaceful now, when you look back.
One flaw of the game is that it purports to represent a neoliberal against a populist regime, when we have a neoliberal leading a populist regime currently. The ideologies are off. You want satire? Imagine Trump lost to Bernie Sanders, and satire the supposed authoritarian socialist regime of Sanders as a neoliberal protaganist. You can poke fun at both sides and its completely ridiculous since it didn't happen...
but it could have.
Now if you excuse me, I have to daydream about what if Bernie Sanders was president for a while...