Simple first pass solution with minimal tools. Only saw one other use this same method. It works for this data set, but might not if there is a different balance of scroogieness. Might be time to learn macros.
Finally getting round to submitting my answer even though I suggested it XD
I chose to have two workflows, the first which would allow people to opt in if they wanted to participate (and also put down a Christmas wish) these were saved to a yxdb and a second to be ran to allocate out across those opted in. Worked really well in the office :)
I know I'm way late to the game, and therefore the Secret Santa theme isn't as timely, but this looked like fun, so I decided to go ahead and tackle it. I ended up with a different set of matches than the included solution (1 the same, but the other 25 different), but I believe my solution meets the criteria. However, I'm not 100% sure my solution is foolproof, if some higher scroogieness scores made a solution harder to come by.
Unless I missed something, this was probably the simplest of the beginner-rated challenges that I've seen. My solution is similar to Patrick Digan's.