The orange set is the key. Jail is the most landed-on space in the game (because you can land it on so many ways - Just Visiting, Go To Jail, drawing a Chance card, rolling three doubles), and the orange set is six, eight and nine spaces from jail, all of which are highly probable totals of two dice. Get and develop the orange set early and the game is basically yours.
 
The game mechanics still suck though, because once you start losing you are likely to keep losing as you have to mortgage, sell or trade your properties to keep playing, which reduces your source of income, and before long you’re spiralling into bankruptcy.

I actually like Monopoly, but that might be because I keep winning.

I don’t think I ever played a monopoly game that didn’t either end with mild yelling or “This shit is getting boring. Who ever is ahead wins. Let’s go do something else.”