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I was wondering if anyone else struggles too actually make money in this game cause i can't seem to get out of the red for very long let along even get close to the lone amount you are given in the beginning of the game.

that happened to me on my first run and ended up bankrupting hard. the trick I used in the most recent run that is going practically infinite is to try and buy the items at about 60% value and sell for 130%. doesn't always work, but you can usually make bank that way. (rip em off)

It's just a game :D don't be afraid of haggling high. Also, pay some attention to how girls start conversation, if they are in bad mood or in hurry, they wont haggle - 1 or 2 chances to give a sufficient price. It is good to invest a few bucks in to first levels of charisma and proficiency skills. Trying to get laid in few first days is not good idea.