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Weclock: do you have to buy a copy of the game from GOG.com?
Can you use a previously bought copy?
Will the Winner be mentioned in the upcoming newsletter?

Yes, you have to buy the game from GOG.com to enter the contest.
As for mentioning the winner in the next newsletter, we'll think it over, but that's a nice idea!
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Weclock: does it say in the documentation how to take a screenshot or does it have to be done with a 3rd party application? My Macbook doesn't have a prtscrn key, in order to get that you have to press a number of keys and I typically use third party software because I can map ss to a different key.
Also, can you only send in your times once or continuously play and keep sending the screenshots of the faster times?

You can use a 3rd party application to take the screenshot.
There is no limitation of how many screenshots you'll send us, but it might be a good idea to take the screenshots after all your races and send us the one with the best time!
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hansschmucker: Well, it's official: I suck at time trial. 0:48:79

practice makes perfect :)