When a guest wants to extend their stay, you either have to change the current reservation or create a new booking.
I would love to see a feature where we can send a quote out to extend a guest's trip and not block the night unless/until payment is made. At that point, the existing reservation would be changed and all departure messages moved out to the new departure date, keycode extended, etc.
As it is, if you change the current reservation, you end up changing the departure date before payment happens. I don't like to block extra nights until payment is made. I have had some guests ask to extend, but then change plans again at the last minute and not actually extend.
Creating a new booking for the extention is also problematic, because I need to skip certain messages on both the current and the new booking to avoid duplicating messages. A new booking also requires a new keycode on my lock, which is different from the current keycode.
It seems like there could be a happy medium where you could create a quote to extend the original booking (at least when it is a direct booking and not through VRBO / AirBnb / etc.)
For direct bookings (including Vrbo bookings, which as an integrated partner are effectively the same as direct), I just confirm with the guest that "the extra night will be $X, shall I go ahead and extend?" and once they say yes, then I just extend it and charge their card at that time. I don't make them manually go in and submit payment themselves, since I already have their card on file.
I agree that the process/UX could be a little smoother all around, though.
How often do you face these issue for extended stays? Is it frequent?
Often enough for it to be an inconvenience. I send out an offer for a discounted night if I have gap nights. Most of my business is regional at this house; it's easy for people to extend when they are driving home.