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I think NLP technology should be used for your project :) I plan to integrate Gorse with NLP, but it might take years to implement it.

NLP is what I was thinking too! To be frank right now I'm just fixated on the problem and the approach to solve it is still in nascent stages.

I think NLP Gorse would be a very valuable addition and agree that it would a huge effort to do it properly.

You're welcomed to comment about Gorse or anything else in the aforementioned thread as well if you have some suggestions to address the problem.