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I have an example for you today of me buying Giant Wintersday Gifts for profit. You can absolutely flip them if you buy now and sell them later in the season (or their contents), but I'd much rather try to make gold now. Here is my first experiment with them so far, buying early on a Saturday morning.
Part of my strategy involved spamming refresh until the gifts were close to 2 silver each. No matter what you get an ugly wool sweater, so you always make back half the silver you spent if you buy at my price range.
First Attempt: 38 Silver for 18 Giant Wintersday Gifts
15.55 Silver for Drops of Magic Glue
19 Silver for Ugly Wool Sweaters
3.85 Silver for Flawless Snowflakes
Result: 38.4 Silver back (.4 Silver Profit)
Yes, I only made .4 silver, but there definitely appears to be an opportunity here for profit throughout the holiday season. On Monday morning I will be buying these things like crazy, emptying the contents, and then selling them by Friday of next week. It's all about being patient, as these items are MOVING FAST. Their prices fluctuate ridiculously quickly, and it makes the difference between profit and loss.