I don't want to pick on Jo's comment, but I noticed a trend on these pages suggesting Kurt has it 'easy' compared to Steve - ideal weather, riding downhill with a tail-wind, etc. Alicia's videos suggest Kurt experiences extremes of weather that we rarely if ever see in the UK. Also Kurt spends a lot of time riding loops, which I put down to the poor riding surface and heavy traffic on most roads he encounters, so when he does find a nice smooth quiet road he tends to stick with it - even if it cancels out the uphill/downhill and headwind/tailwind factors.
As for stopping at night, both riders face the same decision on whether to pass a comfortable bed and do an extra loop.
The terrain and conditions are different, and each rider tries to make the best of what they know based on 30+ years of cycling experience. But I think we (the gawpers, as opposed to the riders) should remember any “advantage” does not add or subtract one inch from the distances riden.