I think you writing level is good, the story has potential. What I would say is usually in rebate or novels like this we see MC get rich and then progress in life. Here he got money but he so scared that he didn't even buy house. He could buy a house in the girl name for big rebate. Like he can buy a building and construct a pub, but having other assets is a risk? I hope this points out the issue, I would prefer if you could stop this again and again with government threat of having them on his back.. he drives a good car own a building and bought a Lamborghini for a girl but can't buy assets for himself. This logic is a little half based. Also he got good memory skill so he can study again (like you mention in the start what he was thinking to do) here you can add a college part and younger women. (I have read till ch 71, would keep reading but this stuff pointed above annoys me a little. Please try to change it)
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LIKEI thought about all of these things, but that would be moving too fast. Imagine a millionaire just randomly buying a girl a house in her name after barely a month. It would put anyone on guard and think he's using money to make up for his lack of charm. I personally didn't want the "simp" title even if his system allowed him that liberty. This is the same reason I didn't make him just spend on OF models and what not. I want a story behind it and this was why I also gave him a cap in the beginning with the whole establish a source of income thing so I can make this a plot driven story as opposed to just smut if that makes sense.