Trigger Booking Field Criteria - Check In Check Out Non Standard Time

I have various templates and triggers that upsell late departure and or early check-ins.
As the date gets closer to arrival a guest is offered an increasing discount off their late checkout fee, 30% 50%, and finally 60% the night before check out.
So when a guest responds to the late check out template offering 50% I update the checkout time in the booking and charge the card on file.
Would it be possible to have a trigger option that looks at the arrival and departure time and not send the template if the arrival and departure time is different from the standard set for the property?
So a booking field criteria of Check-Out Time = All the standard Operators > + < >= Than Standard Property Check out time.
Similar criteria would be applicable for early check-in upsell email templates.
I can skip further upsell messages once they have booked in for a late check-out. But skipping messages manually often gets missed. Its awkward with the guest if they receive more messages on something they already have.

I figured a temporary work around by creating tags.

Late Check and Early Check in tags. If these tags are not present on the booking  emails  will be sent. So if I sell a late check out I can manually tag and the upsell emails won't be sent. It saves a bit of time rather than manually skipping all the emails. 

The original request remains as it would avoid manual tagging.

I would be nice to have this automated within OR so that the guest can simply do the paperwork.

I found this topic b/c I am looking to do the same thing, but I see this feature request as more of master capability across trying to automate a lot of manual processes. To me, it seems OR is missing the way to automatically tag bookings based on events. My biggest headache right now is every guest (several properties) seems to want to request early check in and late check out, so trying to figure out a way to charge, but need to automate it all. 

[Another topic was closed as a duplicate of this topic (Email Trigger based on check-in time (standard or custom))]

[Another topic was closed as a duplicate of this topic (Allow for triggers to be tied to flexible check-in times (not just standard property check-in time))]

[Another topic was closed as a duplicate of this topic (Early Arrival Late Checkout Trigger)]

To add a little flexibility, can we add trigger timing to align with a booking's check-in time? In my specific instance I'm looking for my SMS check-in welcome message to be sent one hour before check-in. This works fine as long as there's not an early check-in, in which case it becomes a manual process of remembering if the guest requested early check-in and manually sending my SMS welcome message with access codes. Would be great if we could automate that with a trigger tied to the guest's check-in time we stipulate with their specific booking.