There seems to be a tension between pattern matching and judging others favorably/reading their words charitably. How can we resolve this?

I'm not sure at all how to resolve it... or if a resolution is even really possible. The problem I see is that we cannot control how another person is going to pattern-match on our own ideas. We can try thinking about potential bad-patterns is might accidentally match to. But that takes a lot of extra work on our part, and still won't reach everybody.

Still, I think it's worth considering for some thing that have already been proven to be controversial (and easy to misinterpret), such as the field of PUA.

I can tell you what he default pattern is there. As a woman, PUA matches as "these people are trying to manipulate my own flaws to get me to sleep with them." along with "They don't care about me, just the "score""... neither of which is appealing to a woman and makes her feel uncomfortable in the presence of people that say they are a part of that scene.

now - these patterns may or may not have validity... but if we want to attract more women to the group.. we'd be wise to either not talk about the things that match awful patterns such as these, or do as you suggested and taboo the words that auto-match against them, and instead talk specifically about the non-awful aspects of the field (eg self-confidence or social-skills building exercises) - especially where they have gender-balanced benefits.

Anyway - this is a long-winded way of again saying that I agree with you entirely.