One notices that this is listed as philosophical whereupon did I feel sadness at the fact there isn't a high scores tab but disappointment is a part of being human after all.
Call yourself Kitteh. Choose fighter, working class and training. Unequip and sell all of your stuff and always sell stuff once you get it. Always use the forest holiday as this will take away all of your stress in one go and it might give you a stat boost as well. Start off by working as a stablehand and get it to 100. This will raise your dexterity so you will be harder to hit and it gives more money than construction. Then go working in construction and get that to 100. Now keep on studying Combat until your combat attack and defense go to 100, if you need more money to get the studying done then be a night guard, it's easier to do if your dexterity and strength are higher so that's why I recommend not working as a night guard until you have construction and stablehand at the maximum. Once your combat attack and defence get to 100 keep adventuring until you find all of the dark blue chests (see Psychomatic's comment for their locations).
Buy lounges and put them at the middle of the school. The only other building you should buy yourself is a classroom. Once you have built as many lounges as possible buy farmhouses and then once you have 2 farmhouses upgrade your classroom and keep upgrading it until it gets to the max.