The problem: We run multiple short-term rental listings, and our main cleaner can only handle one location per day. Our pool house always gets priority to come first. I found our cleaner double-booked at two different locations on the same checkout day more than once, and each time I had to catch it and reassign the tasks by hand. After fixing them manually, I wanted a rule that would catch these before they turned into a problem.
The rule we wanted:
- The primary cleaner always gets the pool house first.
- Never book them at two different locations on the same day.
- If there’s a conflict, they keep the pool house and the other job goes to the backup cleaner.
- Our other building has several units that can be booked separately or together. Those all count as one location, so cleaning several units there on the same day isn’t a conflict.
What we found: Hospitable’s built-in task rules assign a cleaner per property, but they can’t apply conditional logic (as far as we know) like “if they’re already booked elsewhere that day, swap them.” So we used Claude with the Hospitable connector instead.
How we set it up:
- Claude pulled our teammates, properties and the next 4 weeks of cleaning tasks through the Hospitable connection. It confirmed it could reassign tasks between teammates.
- It checked the current schedule against the rules. Since I’d already fixed the existing double bookings by hand, there were no conflicts left, which confirmed the schedule was clean before the automation took over.
- It created a scheduled task that runs every morning. Each run checks the next 4 weeks of cleanings, groups the multi-unit building as one location, and flags any day the primary cleaner is booked at both locations.
- For each conflict, it proposes keeping the primary cleaner on the pool house and reassigning the other job to the backup.
Testing safely: For the first 4 weeks, every change waits for my approval. I get a push notification, review the proposed swap and say yes or no. There’s a reminder set for the end of the trial to decide whether to let it reassign automatically and just report what it changed.
Takeaway: If your scheduling rules are more complex than “this cleaner for this property,” a daily automated check through the Hospitable connector is a practical way to handle them. Run it with approvals first until you trust it.