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To the original question, having both wheels touch is impossible to work with in the real world because uneven surfaces will frequently result in the stand not touching the ground at all.
Don't know where abouts you live, but this has never been an issue in the years I've been a cargo bike mechanic in Seattle.
JVBulman-
Bro do you even Britain under Tory rule?
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I've never had an issue with that in the UK either. If you park a Bullitt on uneven ground, one of the wheels ends up not touching the floor, as opposed to the stand. To be honest that can work a bit better than both wheels AND the stand touching the ground because as people have mentioned, if you're on a slope or it's particularly windy and if the stand is worn down at all (as they tend to be quite quickly), they have a tendency to want to roll off.
pdlouche
ltc
To the original question, having both wheels touch is impossible to work with in the real world because uneven surfaces will frequently result in the stand not touching the ground at all.