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Based on my own experience as a club treasurer managing a shoestring budget I'd just stick with Quicken, even if your guild has to spring for its own copy. There's much to be said for keeping things as simple as possible (and in my case, I had a successor who really needed things to be simple). I can't speak to YNAB, but I tried GNUcash for our stuff at home after MSMoney faded away, and I didn't find it nearly as user-friendly as either MSM or Quicken. But if you've got time to figure it out, it would probably be a decent alternative.
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