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When I take the new Stock market , the rules say I move up the stock market, and then earn a personal payout. Just to be clear, if I am at the top of the track already, I would earn the personal payout twice, right? (Once for advancing off the chart, and then again for the power.)
That's how I interpret it. Plus it wouldn't make sense if it didn't. You could earn a personal payout twice by using the ? Tile before reaching the top, and again by trigger your last stock market action when you are at the top. So you should be able to trigger a double personal payout as you described.
However, I do think (but not sure) each personal payout would be executed individually. So you would have to resolve all 6 bonuses before resolving all 6 bonuses the 2nd time. This could matter.