Great points. The restaurants plugin you cited is using an outdated API. The new API uses triggers rather than a switch statement, which requires a combination of a Command and an Object to trigger a plugin's response (see plugin_weather for the modern API). This helps eliminate many false positive matches. But to your point, you're right, that scenario would still trip it up. I plan to add support for matching on n-grams going forward, so you could define different behavior for "street number" vs "phone number" and it would match the longest (in most cases the most specific) option when multiple matches are detected. It's actually similar to how many routers work.

You're also right that Abot plugins as they stand now do not improve or learn automatically over time. I've done some work on a training system which will enable a Facebook M or Magic-style human-aided training backend. It'll be a plugin just like any other which will eventually be hooked up to a neural net with optional centralized training (so you don't need a GPU rig or tons of data to get started). An early version of that is probably going to be ready going into June with the v0.2 release.

Thanks so much for the feedback. I'd love to continue this discussion and find ways to improve plugins and training. If you're interested, there's a mailing list here: https://groups.google.com/forum/#!forum/abot-discussion