By far in regular Monopoly the best Monopoly are the Oranges (St. James, Tennessee, and New York). If you get that monopoly and then use your cash to get at least 3 houses on that monopoly before anyone else has more than 2 houses on ANY property, then you have a 75% chance of winning the game.

The reasons: 1) There are two double numbers from Jail that would force you to land on St. James & Tennesse. 2) 6,8, and 9 are all common numbers on a die 12 and those are the positions from Jail for the Oranges. 3) From Start, those properties are position 16, 18, and 19. Although not as common, not the worst positions from Start.

Park Place is one of the most worthless properties, because it is impossible to land on it by rolling a 7. Due to this always develop the higher uneven housing development of Boardwalk and Park Place on Boardwalk. The advance to Boardwalk card is the only reason the Dark Blues end up being worth developing in the long run if you can survive long enough for them to pay out.

The light blues are always worth developing fast as you can. It won't win you the game buy itself, but it can cripple your opponents so that they never have enough cash to develop their Monopolies. If you need to trade to get your Monopoly, it is better to wind up with the Light Blues and/or Oranges and ask for cash to cover the difference of the property you are giving up for it. Then the next thing you do is put as many houses as you can afford immediately on the Monopoly. If you have the Light Blues you need 4+ houses on each to cripple your opponents ($600). If you have the Oranges you need 3+ houses on each to cripple your opponents ($900).