People tick all manner of boxes inside their heads while they're doing things. It's when they expect others to be ticking those same boxes that it gets a bit weird.
I'd see Steve's record attempt as a management problem. It was originally envisaged that support would be 'crowd-sourced' and a timetable drawn up of where he would be and when. That seemed to prove unwieldy, and was abandoned after the accident.
The optimum solution would seem to be the Kurt approach, but Steve cycles for longer, so you'd need two Alicias, and it would be on a formal, rather than intimate, basis. That would mean weekend cover, and once you start moving to a warmer place, it becomes unworkable.