Hmm, good question. Realistically I have a lifetime's backlog on steam already, don't need any more. But as long as I'm here... :)
1: If the points are overflowing, i.e. a bundle explosion that didn't make the bundle list yet, I will enter whatever sounds fun, even if I know I won't have a chance to play it for months.
2: Don't enter many of these. If I really want that game and love it, I already bought it... :)
3: Puzzles are fun, aside from the brute-force kind. A random fact about your life that only you know, yes it's obvious to you, but "What have I got in my pocket?" is neither a riddle nor a puzzle... :) However, I do enjoy the tricksy ones that only appear to be brute-force because I overlooked some hints. There are some wonderful puzzle makers around here, where it's more fun finding the giveaway than winning it... :)
a: Some giveaways I enter because the game sounds crazy, never heard of it before, maybe I played it 10 years ago and never finished it, random things like that. Mission: Runway? Snuggle Truck? I have to enter, just for the possible terror of winning it... :) Duke Nukem 3D, I played it years ago but never finished. Honestly I'd probably never finish it today either, but it would be fun to relive those old memories. Blood Dragon? Looks insane, I'd never buy it but I'd certainly give something that crazy-looking a try... :)
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Because:
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