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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.
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.
Sort the list by Scrooginess. Use the sample tool to split the first half and last half into separate data sets, then reverse the sort on one half and do a join on record positions. Sum the two scroogieness columns. You'll have unique pairings and the lowest set of pair values