The figures directly from the GPS are misleading (and the link you include only has Steve's restart data). By my calculation Steve has been riding with about double the elevation gain of Kurt. This is what I said in the other place:
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Elevation gain is tricky to measure in a reproducible way because it depends on how frequently you record elevation and is also more sensitive to GPS error (see the few days of atmospheric climbing for Kurt when his GPS was on the blink).
To compare more reliably, I've polled elevation every 5 minutes through the year for both riders and calculated the elevation gain from the change between those 5 minute elevation snapshots. This absolute figure is a little lower than Strava's (which poll elevation more frequently), but is consistent between riders so provides a good basis for comparison.
Over the year:
Kurt has gained around 113 vertical km in elevation, while Steve has gained around 235 vertical km. Standardising by distance covered this works out at around 0.94m elevation gain per km for Kurt and 2.25m per km for Steve. So Steve has been riding approximately 2.4 times as 'hilly' a terrain than Kurt. To put those figures in the context of typical UK riding, Audaxers would usually assume around 10m per km marks the boundary from gently rolling to hilly. So both are generally riding easier terrain than most UK rural riding.
To see the daily variation, I've graphed both riders with the thick line representing the 7 day rolling average elevation gain.
View attachment 114734
You may notice that Kurt's Wisconsin riding was his hilliest, but was still less than Steve's typical routes thought the year.