Personally I work at the Cafe just once to get around $500 - $1,000 at the very beginning of the game. Take lots of photos of Anna and don't buy anything until you receive Car Key from Josef and go meet Mario at the Garage on Thursday. Accept his offer to work for him and go to his Villa to start Mario's Questline ( Resume Checklist Minigame ).
You can do the Resume Minigame 3 times ( once a week ) and you'll receive $2,000 for each successful minigame ( $6,000 in total ).
Then after you finish the last minigame, Mario will talk to you regarding his wife, Katarina and he wants you to fuck her. Accept his offer, fuck Katarina twice ( once a day ) by speaking to Mario first and you'll receive $2,500 ( If I'm not mistaken ).
After that, he'll tell you how he wants to divorce his wife and fuck his daughter, Emma, instead. He wants you to help him corrupting her, accept his request and go to the Sauna ( once a week ) and tell Emma that she's beautiful and perfect until she becomes horny and wants to have sex with you.
Carefully pick the Mario Sharing Route dialogue and tell Emma that her Dad wants to fuck her as well. Then speak to Mario and tell him that she is ready. Next week, go to Sauna again and Mario will join in the fun and you'll get $ 3,000 from him.
You can get $5,000 from Mario by Betraying Sofia Route, but you have to play the scenario carefully if you want to get the money and unlocking the Guest Room.
In the end, just by progressing Mario Questline alone will give you around $11,500 ( Bonus $5,000 if you choose to betray Sofia ) and use that money to slowly, but surely progressing whichever Anna Route you chose.