Hi @Ben Choy !
Trello's super flexible, which is awesome, but it also means there isn't a one-size-fits-all answer for all tasks, including yours of managing vacation days. You can definitely set it up in a way that works for you, but it might take a bit of creativity and tweaking.
If you're looking for a more tailored solution or need help setting things up just right, you might want to check out our Atlassian Solution Partners. They're pros at this stuff and can help with migrations, integrations, training, and all that good stuff. Plus, they can help you configure Trello to fit your specific needs.
Here's a link to find a Solution Partner near you: Atlassian Solution Partners.
Hope that helps! Let me know if you've got any more questions.
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