Thanks for this @chris.williamson1996,
Really interesting suggestion and I’ve reworked the workflows to make it function as you’ve laid out in addition to incorporating @adamhholmes suggestion . However, after much testing, it still doesn’t reliably work to my utter confusion. It seems to work at normal speed, but not at step-by-step speed, which really confuses me and makes debugging of other issues rather impossible.
TL;DR: Slow Mode and Step-By-Step mode seem to have a bug at the Bubble level that normal mode does not that makes step-by-step or slow debugging nearly impossible.
The high level workflow is now broken into three major (error prone) sub-stages:
In the first, I have triggered the pre booking checks, and added before & after states, as per your guidance.


Once the final “Ready for Booking” Error state is changed to a yes, and only when it is yes, should the next stage, the booking, begin:


Despite two levels of checking whether the condition has been met, the booking somehow still happens. I’ve isolated it to the booking and not the error states, because removal of the booking stage from the workflows doesn’t result in a booking.
On the debug step by step mode, it claims to work exactly as you said it would: the booking workflow does not get triggered. However, the reality is that it does get triggered even though it shows as not triggering in debug step by step mode. Weirdly, in the normal mode, it functions (so far) as intended.
I make a booking:

The top level workflow is triggered:
And before it gets to the trigger booking, it’s already made the booking:
This seems to be an issue with the step-by-step mode of debug. With the normal mode, the issue seems resolved by following what you @chris.williamson1996 and @adamhholmes said in combination. The bubble loading bar still chugs on even in debug step-by-step mode.
To test this, I made shapes appear within each workflow and disappear within the next workflow, so that if the workflow was entered, I’d know, and I’d see if the same actions responded differently in normal mode vs. step-by-step mode.



Different shapes appeared depending on the mode chosen. In normal mode, the shape that was supposed to appear in the first trigger and disappear in the second trigger (shape jemima) never appeared at all. The shape meant to appear in the second trigger and disappear in the third trigger did just that (shape williamson). The shape meant to appear in the third trigger and disappear at the end of the workflow (shape adam) never appeared at all.
Slow mode and step-by-step mode result in a different sequence (and thus different boxes). In Slow mode, the first box in the first trigger (shape jemima) appears. Slow mode / step-by-step mode invariably results in an error being created, and thus the condition for triggering the other steps not being initiated, the other shapes for trigger 2 (shape williamson) and trigger 3 (shape adams) are never called, and shape jemima is never hidden.
TL;DR: Slow Mode and Step-By-Step mode seem to have a bug at the Bubble level that normal mode does not that makes step-by-step or slow debugging nearly impossible.