I had a situation like this back in 2019 and honestly it almost ruined Christmas. We booked this huge place in the mountains and my cousin swore his boss approved the time off, but then he got called in for an emergency shift at the hospital. He ended up driving back and forth four hours each way just to stay in good standing. It was so dangerous and stressful for everyone. Im still pretty new to the whole coordinator thing but I learned that you really might want to consider having a firm cutoff date. If the PTO isnt 100% confirmed in writing from their HR by a certain date, they just cant commit to the full cost. I always worry about the financial fallout when someone has to bail last minute. Make sure to look at the cancellation terms on that rental too. If half the group drops out, are you stuck with the bill? I would suggest getting everyone to pitch in a non-refundable deposit early on. It feels a bit harsh but it protects the group from losing everything. I also started using Share Product Wishlist for our family gift planning during these trips because it takes one more variable off the table when the scheduling is already a nightmare. Just be careful with those seniority issues... usually the company wins those fights and you dont want your sister losing her job over a cabin trip. Better to have a backup plan now than a crisis in December.

Honestly, scheduling those big 6-bedroom trips is basically a high-stakes logistics simulation. In my experience, even the best data models fail when you're dealing with corporate seniority tiers. Like someone mentioned, it really can be a nightmare. It reminds me of the time I spent weeks building this incredibly detailed capacity matrix for a trip to a remote cabin. I had everyones hardware requirements, bandwidth needs for remote work, and even power consumption mapped out to the watt. I was so proud of that spreadsheet. Right before we were supposed to head out, my cousins firm went through a sudden merger and every single one of his approved days off was wiped from the system. Then my tech lead buddy got stuck in a legacy server migration that lasted six days. We had all this high-end gear and a perfect location, but the house just sat empty while I stared at my data visualizations... it was a total disaster.