That's a difficult thing to do automatically. The simplest thing you can do is look at the date -- any more than 3-6 months out of date (ie more than 2 GUs out of date) and the chances of it not working go up a LOT.
I'm not sure something where users could mark a UI as not working would work well either. We see lots of folks posting that suchandsuch doesn't work and then it turn out that it didn't work because they installed it incorrectly, rather than the UI not actually working.
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