got every medal except winning the game, which i would say is pretty much impossible; not sure how that one guy managed it.
basically the only meter that matters is the happiness meter. once that depletes it's game over.
you can be completely poor and tired at any time and it would be fine, as long as happiness is over 1.
right off the bat, you can gain happiness by sleeping, watching out of the window, painting or drinking. painting and drinking both require money.
you can only make money via working, and even then most of it is lost between the time you need to recover stamina between days. (ignoring the requirement for mashing, which makes it worse).
eventually, sleeping stops making you happy. if your happiness goes below 50%-ish at any point, you start being depressed, at which point looking out of the window also stops making you happy.
basically after you get far enough into the game, you can only gain happiness with money, and the rate at which you make money is always slower than the rate at which you recover happiness, which means a guaranteed game over.
all of this is only to survive. the actual objective is to completely fill your fame, which can only be done via painting or working (at max efficiency).
basically the only way to win would be to speedrun the game in a way where you prioritise your fame meter at all time, making sure your happiness doesn't reach zero before you eventually lose all your money and can't recover happiness anymore. honestly i have no clue how that's possible.