Since this is my first year of PC gaming in quite some time and I had missed out on the previous Autumn/Winter, let me ask a question. Are the prices for the Winter Sale cheaper or about the same as the Autumn Sale? While I'm sure some stuff -- especially that at 75% off -- has bottomed out, what if something, say, Skyrim was offered for $20 during Autumn. Would there be a good chance or no chance that it might hit $15 for Winter?
I would say 75% is the lowest you'll typically see. There's only a few weeks between Black Friday and Christmas so, if you really want Skyrim on sale and it's 66% on BF, I'd just wait the couple weeks and see. Spend some quality time with your backlog.
Prices on Skyrim have been fairly stable though since I assume the game still sells well. I wouldn't expect to see it at bottomed out pricing yet but maybe I'll be proven wrong.
Best advice I can give is to wait for a price you can afford and think is fair and just embrace your decision. You can make yourself feel much more sour over $3 than $3 is worth when a game goes from 66% to 75% or another place has it a little cheaper or you could have gotten a DLC bundled for the same price. Stuff will always go on sale cheaper. Either a deeper discount or a lowered base price or in a bundle or GOTY edition or whatever. If you're not going to play it today and seeing it for a few bucks cheaper will bother you, just wait because it will
be a few bucks cheaper later on.