Sadly, due to the randomness of the dice roll, on top of the randomness of the square you land on, trying to use strategy in this game has been a nightmare! One thing I would caution people about, remember when you buy turnips you still have to roll on Sunday, and there are no turnip buys on Sunday, so I recommend holding off spending all your money on turnips, it may cost you that day landing on a money point loss which also loses you happy when you go negative. That's about it, all this random luck can make you go from -10,000 bells to 90,000 bells due to that money tree! You can totally win simply on luck on the final roll, even though you were losing the entire game...