Although the pieces move in a circular way in Monopoly, you could think of it (and this is a stretch) that they're actually jumping.
Let's say that "Go" is the earliest that Ben can time travel...how about an arbitrary 2001, and the last square (Park Place?) is 2005 when he is operating Sayid. Just a thought exercise here, folks.
Ben has an idea of where he'll land...roughly. His racecar's not gonna be flung all the way past "Go to Jail" on the first roll, but he'll still have to ask the front desk clerk what neighborhood he's in.
On subsequent rolls, he manages to arrange to have all of the orange properties. This is a metaphor for having "gotten to" Sawyer, his dad, and his girlfriend...or any other group of connected people or events. The point is that he's secured those people/events while Widmore has been working on his own properties.
