I really like the idea of having the gedmatch compare prepared on the profile, or at least available in a DNA tab/section/widget page. My one concern would be implementing it so it doesn't overwhelm either WikiTree or gedmatch servers, especially when first turning it on. Even with "only" 30000 or so DNA tests logged on WikiTree, and only some of those on gedmatch, there would be a lot of profiles that would need a DNA comparison chart.
I don't like the database errors for DNA lack of match, unless it's done only for very close relations. In your example, the two descendants who do not match are 4th cousins once removed. It's quite possible for them to share no significant DNA segment and still have the paper genealogy be correct; a database error here is pointless and likely to cause more mistakes than it does solve actual problems.
I'm not sure how I feel about the idea of trying to automatch people who are not connected. I sort of feel like it's outside the bounds of what WikiTree should be focused on, there's a lot of chances for mistakes, and also it could get very computationally intensive quite quickly. That's probably better left in the hands of gedmatch and the DNA testing companies.