I find myself always sending out the same messages over and over. Now the relatively new 'saved messages' is great, but it would be nice if some of it could be automated, so the relevant information can be dished out at the appropriate time:
1. Booking Confirmation: straight after a booking is made, it would be nice to send a confirmation message to say thank you for picking us, along with address and travel tips.
2. Check-in Reminder: 24 or 48 hour before check-in, a message about check-in time and how to obtain keys.
3. Arrival message: on the day of arrival at check-in time, send a welcome message with house menual, rules reminder, wifi password etc.
4. Check-out reminder: the evening before check-out (say 18 hours before your typical 10~11am check-out time), a reminder of the check-out time, how to return key, and good bye have a nice trip etc.