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if someone only has $300 in cash, and is about to roll into the final stretch (greens and blues) it makes no sense for him to bid at all for Connecticut Avenue
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Maybe, but can't you mortgage your properties to afford these costs? Or are there only certain times you can do that?
And FWIW, I don't think the game really takes THAT long, if you have people who know what they're doing play it. Sure, if it's mostly kids it will take way too long for childlike attention spans.