The city is divided into 4 different areas where you travel between each with the subway:

SOUTH: start, here you will rely on the Soup Kitchen that offers free meals.

EAST: High school (which is free) and College (which costs 100 dollars per day). You need 3 days of school in both before graduating. You don't need a haircut to go to school. The IRS roams the streets in the East. Beware.

WEST: Hairdresser, 4 dollars and last 3 days after your visit. There's nothing else you need in the West.

NORTH: City industries (requires a High school diploma) gives you 100 dollars per day for work. Executive Towers (requires a College Degree) gives you 5000 dollars per day for work. Mutual Funds is were you deposit 10 grand and receive a daily dividend payment each morning.

There is a glitch in the game where whatever appears on the street (bottle, coin or bill) will keep appearing if you pick it up on the left side - immediately go right until it's barely visible to your right and then you go left again, stop to pick it up, go right etc. This is what I do in the beginning, keep looking for the green dollar bill and exploit the glitch.

Day 1: Collect dollar bills off the ground and utilize the glitch that makes the dollar bills re-appear when you cross the screen. I want to spend the day buying 4 tickets and put down 10 $ in the bank account. Never sleep in a hotel - use the free soup kitchen and eat at 6 or 7 pm to last the night.

Day 2: First day of high school. I used to think that you needed to cut your hair in order to attend school. Just found out that you don't a couple of weeks ago. Then back to the soup kitchen.

Day 3: Second day of high school. Same procedure.

Day 4: Third and final day of High school. Then to West and a haircut.

Day 5: First day in the North - job starts at City industries at 8 am, then back to the soup kitchen

Day 6 and 7: keep working that gig at City Industries

Day 8: Start College

Day 9: second day at college

Day 10: Third and last day at College

Day 11: Need to cut your hair

Day 12: Work at the Executive Towers

Day 13: Second day at the Executive Towers and first deposit that creates an eternal dividend.

There you go. So many things to learn about this game and so many different strategies I have relied on through the years. This is the optimal strategy to beat the game as fast as possible, there is no way to do it in fewer in-game days. Of course you could sleep some nights in a hotel to keep the actual seconds passed down if you want to.