Monopoly is a strange game. The only winning move is to play as often as you can!
Monopoly gets crazy. I mean, seriously. Have you played Monopoly? It's one big positive feedback loop: Opponents land on your spaces, they give you their money, you use said money to build houses and hotels, you get more money. Lather, rinse, repeat. If you're the one earning money, you keep earning money. If you're the one losing money, you're forced to sell your siblings to cover the rent on St. Charles Place.*
*When families play, this puts the children at a serious disadvantage, as their parents technically own their siblings already.