I have to agree whole-heartedly if there was an easy way to mark the plugin as working or broken right in the installed plugins screen I would do it without a second thought.

The problem that I think most of us have, as you mentioned above is if it's working as expected we tend to never go back and rate the plugin (or at least mark is a working/broken).

A simple link in the Installed Plugins list right after or around "Visit Plugin Site" saying something like "Does it work? Yes | No" that would automatically integrate with the Plugin repo stats could work. I know this probably is a lot easier said then done, but I think this would be a good fix to help support the plugin developers (and even theme developers if there was similar integration) and make it easier for plugin users to know if it works.

All that said though, I never consider the working/broken stats when finding a plugin just because half of the ones I look at don't have enough data, and those that do have a 50/50 split. But, I am experienced with WordPress - what about the new users or non-tech savvy users who won't try a plugin because they are afraid something will break that they can't fix?

I mean, looking this morning Jetpack and even bbPress don't have enough data to say if it's compatible with 3.61 and they are hugely popular and widely used. No one has come back to rate it since the update. At this moment this data is extraneous because of the lack of participation (users fault) and accuracy (lack of data). If we could get the community involved in an easier, simply integrated way then the value of that data would be what we are looking for now.