Allow Automated Messaging Rules Based on Check-In Dates or Seasonal Date Ranges

It would be incredibly helpful to have the ability to create automated messaging rules based on a guest's check-in date or a specified date range, rather than only using the timing of when a message is sent.

For properties in seasonal destinations, the information we share with guests can vary significantly depending on when they're visiting. Currently, there doesn't appear to be a way to automatically select different message templates based on the dates of a guest's stay.

For example:

Seasonal pre-arrival messages: Send winter-specific arrival information (4WD/AWD recommendations, snow removal, icy conditions, etc.) to guests checking in between November and April, and summer-specific information (lake activities, park access, etc.) to guests arriving between May and October.
Restaurant recommendations: Automatically send different restaurant recommendations based on the guest's arrival dates, since many restaurants in our area operate seasonally.
Seasonal activities: Send information about skiing, snowmobiling, and winter recreation to winter guests, versus boating, hiking, and summer activities to summer guests.
Date-specific information: Send relevant information about local events, seasonal road closures, or temporary conditions to guests whose stays fall within a particular date range.

Suggested functionality:

Add a condition to automated messaging rules based on the reservation's check-in date.
Support recurring annual date ranges (e.g., November 1 through April 30) as well as specific calendar dates (e.g., December 15, 2026 through January 5, 2027).
Allow different message templates to be triggered depending on which date range applies.
Ideally, support check-out dates or any overlap with the reservation dates for information relevant throughout a guest's stay.

The key distinction is that the rule should evaluate the guest's stay dates, not the date the automated message is sent. For example, a guest booking a January stay in August should still receive the winter version of the pre-arrival message.

This would significantly improve the relevance and accuracy of automated guest communications while reducing the need to manually adjust messaging rules throughout the year.