Preventing Checkout

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Hi everyone!

I have a rental shop and unfortunately, there are a very limited number of apps that can handle rentals, and none of them can perform the function I am looking for. I rent board games, and I ship across the US. Since customers pay for shipping during checkout, I need each item in their order to be booked for the same number of days and for the same date range. Every rental app  puts the booking calendar on each product page, and that allows customers to be able to choose different booking dates for every product. None of them can lock in a date range once it is selected. Unfortunately, I have already had an order come through for two different products and two different date ranges for booking. I am looking for some sort of app that can review the dates selected on each item during checkout, and if they don't all match, it blocks the customer from being able to checkout until they correct the booking dates. Any help would be greatly appreciated!!