The only thing that bothers me right now is probably the whole "you can't see all the levels of your skills" bit. Otherwise it's fantastic! Been playing sneakily. If you want a guide to quick, semi-legal cash (even more than you would with the protection racket, and far safer), click the spoiler.
Basically, thanks to garment-making being automated, you can train a small amount of people to make garments for you at a permanent basis. What I did was get 3 people with 9 or higher garment making level, and set them to make expensive suits. Then I have one "nobody" sell them for an immense profit. The only downside to this is that it takes a few game-years unless you want to have more than 3 of the garment makers. In 2017, I was earning insane amounts of money, making around 700 of them pretty suits, which equals to quite a bit.
I would however suggest reconsideration of the whole "selling t-shirts" thing. Maybe it would be more of a business venture than something demanding garment making skill?
If this progress keeps up, this game may very well fall into my top 5 games ever.
Garment makers are more useful by making expensive suits than selling on the street. At the point where selling on the street is profitable skill-wise, you might as well up their juice + skills and make them fix you up expensive suits by the hundreds per year, and then t-shirt selling kind of loses its value considering all the additional benefits of being able to USE what you make for infiltrating areas. I could be wrong on the numbers here; but a garment maker doing what I put him to do earns around 100 000 a year if skill-level 9 or higher...
What I was thinking was making the business skill determine how many t-shirts you can sell in a day, and garment making deciding how many you can MAKE in a day - then again, this is STILL kind of redundant, and one might as well sell lemonade.
If I am making no sense, I apologise. I'm somewhat tired, and for some reason things seem to be "zooming out". Not a good sign for the coherence of my posts. Hopefully this clarifies some?
You don't need to spend years teaching your garment makers. Hunt around in upperscale neighborhoods and you can find clothing designers who already have massive skill.
But if you want the REAL moneymaker:
Get someone with massive persuasion, founder can work if you're taking the path but other options are lawyers/judges or converted media figures but you'll need to gain juice so you'll have a high persuasion limit. Go somewhere downtown with lots of liberals like the courthouse or apartments. Discuss issues with every rich liberal you see and moderates too while you're at it. Get a massive mob of yuppies following you to the homeless shelter the next day to hear you preach the holy word of liberalism. Hold "B" for a while until they're all ready to fight for the cause but rather then making them fight, just take their money. It takes a little rl time but doesn't take too much game time and it should be plenty of cash to last you a while.
People with redneck professions (yokel, hick etc.) that I've seen are always CSS members.