There is an old Polish proverb that says, "A twisting road will take you to Warsaw, but you won't be bored."
“The hard way” is a term from the dice game craps, which is played in the episode (set largely in a casino). It refers to the roll which is the sum of two identical dice. In craps, these are even numbers 4, 6, 8, or 10. One might roll a 6 as 1,5 or 2,4 or 3,3 or 4,2 or 5,1. Only one of these possibilities is the sum of identical values, while there are several combinations (collectively referred to as the “easy way”) that are the sum of differing values. There are fewer hard way rolls than easy way rolls, hence the name.
Jonathan Jackson is a reclusive billionaire who lives on the top floor of his casino. No one has seen him in years. As a rough sketch, this is the lifestyle of billionaire Howard Hughes near the end of his life. In Hughes case, this lifestyle was a consequence of various illnesses.