Alright I liked the concept of your story. A shameless layabout who likes to take short cuts and want to be king of all trades. Me being that demographic, I can guarantee you that I would not start with being a farmer. I would like to do stuff that I can get the most out of with least amount of effort and time wouldn't matter to me. I don't know why he is in such a hurry to get level 10 fast. Slow and steady is the game of the lazy king. I would probably start with gambling. get some money through black jack. Not a lot but $100,000 or so through a couple different casinos than get good in poker and his money trouble goes away. Money can't buy happiness but neither can being poor and money does help in many ways like helping his mother. After that slowly learn everything that he needs to.