Yes registration is done on request which generally should not impose a problem.
The problem here is more in the way I’ve implemented the CheckTrigger condition task, in the sense that I do not actually register it to OnTriggerStay, but rather only use the OnTriggerEnter to determine if stay is true as well.
So probably a better approach would be to actually also register and use OnTriggerStay as well, since that is what we really need to check here in the first place: