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.

tbh i've done this for fifteen years and unfortunately the 'one big cabin' dream is usually not as good as expected when you factor in corporate nonsense. people backing out last minute and leaving me with a huge bill has been a constant issue. its disappointing how unreliable work schedules are these days. if you want to keep costs down and avoid the stress, you gotta change your strategy:

• dont book the massive place until at least 70% of the group has written pto approval.
• make everyone put down a non-refundable deposit to you personally. it sounds cold but people suddenly find a way to make it work when their own cash is on the line.
• look into smaller adjacent rentals instead of one giant lodge. it usually ends up cheaper per person and you dont have to worry about one person's on-call shift ruining the whole vibe. basically, quit being the family's insurance policy. if they cant commit, they dont get the mountain view... it sucks to be the bad guy but your wallet will thank you.

Regarding what #3 said about "tbh i've done this for fifteen years and..."

• I have to agree with that sentiment. Unfortunately, I have had major issues with the single-unit booking model for large groups because the risk of a single point of failure is too high. If one persons PTO is denied or they get stuck with a shift, the financial burden on everyone else spikes. Late to the party but I usually compare two specific strategies for these situations:
• Modular Strategy: Book several smaller units close to each other. Pros: much higher reliability and individuals can cancel without ruining the budget for the group. Cons: you lose some of that shared common space for late-night hanging out.
• Core-Funding Model: Only book a place that the three most reliable earners can afford on their own without help. Pros: zero financial stress if others drop out last minute. Cons: you usually end up in a much smaller or lower-quality cabin than you actually want. Honestly, the modular approach is the only way to handle these corporate scheduling conflicts without losing your mind. It is not as good as expected to have everyone under one roof, but the reliability data just doesnt support the big cabin dream anymore. Its basically a gamble at this point.