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so I'm sitting here thinking about buying Alan Wake (or not) and while I want to try the game, I'm a little tight on cash and I'm not sure if I'd actually like it.

so in the back of my mind I'm kinda going, "ehh I'll skip it till later on when I've got more cash on hand the full price drops" but then it hit me; will the price drop?

all of gogs previous releases never really change in price, mostly because they are rock bottom anyway, but what is gonna happen 6-8 months from now when these newer titles have dropped below the current GOG offering?

(P.S. I'm not sure if this has already been discussed .....)
Its price will probably drop at some point. Alan Wake is a relatively new game, and thus is being sold at a higher price, but in a few years, I would suspect that it will reach the $10 line in most online stores, GOG included.
That's a damned good question, I don't know if even GOG knows the answer at this point (though it's either contractually possible or not, they probably know that).

Also, will they be eligible for the 50% off big summer and winter sales? Who knows, one would assume "yes" since they will be on other store fronts.
Not before 2-3 years thought I think ^^'
I think it's up to publisher/devs.
Some prices have dropped in the past. But you're right in that it's not commonplace. It's hard to say whether or not new games will drop in price as regularly as they do elsewhere. But it's not impossible.
There have been some price drops in the history of GOG (for example in the case of Beyond Divinity, Port Royale 2, Patrician 3 or Tropico Reloaded, to name a few - actually, at one point, a "40% off a number of strategy games" promo was the introduction to a permanent price drop).
But I1m also curious what the case is regarding new (or new-ish) games. Or games from 2005+, for that matter - we have Rollercoaster Tycoon 3 for $20, and while I'm sure the game, bundled with the two expansion packs, is worth that much, it makes me wonder if games will still be sold for $20+ even if they are 5-6 year old.
They better get used to it because newer games do drop in price, and will drop in price on other portals.