I'd like the LW culture to be as much on the ask side as possible, and punishing for voicing hypotheses (when they are wrong) seems to push towards the covert uninformed guessing.

Sort of- punishing guessing also makes the "what are your goals here?" question more attractive relative to the "I think your goals are X. Am I right?" question.

That said, I agree that discouraging voicing hypotheses should be done carefully, because I agree that LW culture should be closer to ask than guess.

The effect it has on me is for example that I've just added the "appear to be" disclaimer in the preceding sentence, and I'm somewhat afraid of talking to you about your beliefs or motives.

Thankyou for adding the disclaimer. My motives in that comment were not primarily about punishing the public declaration of false, negative motives and instead the following of practical incentives I spent three whole paragraphs patiently explaining in the preceeding comment. It would have been worse to make an unqualafied public declaration that my motives were that which they were not, in direct contradiction to my explicitly declared reasoning, than a qualified one. After all, "appear" is somewhat subjective such that mind of the observer is able to perceive whatever it happens to perceive and your perceptions can constitute a true fact about the world regardless of whether they are accurate perceptions.

I would of course prefer it if people refrained from making declarations about people's (negative) motives (for the purpose of shaming them) out of courtesy, rather than fear. Yet if you don't believe courtesy to apply and fear happens to reduce the occurrence that is still a positive outcome.

Note that I take little to no offense at you telling people that I am motivated to punish instances of the act "mind read negative motives in others then publicly declare them" because I would endorse that motive in myself and others if they happen to have it. The only reason the grandparent wasn't an instance of that (pro-social) kind of punishment was because there were higher priorities at the time.

I recently made the observation:

That's an untenable interpretation of the written words and plain rude. (Claiming to have) mind read negative beliefs and motives in others then declaring them publicly tends to be frowned upon. Certainly it is frowned upon me.

That is something I strongly endorse. It is a fairly general norm in the world at large (or, to be technical, there is a norm that such a thing is only to be done to enemies and is a defection against allies). I consider that to be a wise and practical norm. Thinking that it can be freely abandoned and that such actions wouldn't result in negative side effects strikes me as naive.

I took it as a personal favor when the user I was replying to in the above removed the talk about some motives that I particularly didn't want to be associated with (and couldn't plausibly have been executing). (If I recall the declared motives there implied weakness and stupidity, both of which are more objectionable to me than merely being called 'evil'.)

punishing for voicing hypotheses (when they are wrong)

People tend to hypothesise negative motives in those they are in conflict with. People also tend to believe what they are told. Communities are much better off when the participants don't feel free to go around outright declaring (or even just 'hypothesizing') that others have motives that they should be shamed for---unless there is a particularly strong reason to make an exception. The ability to criticize actual external behavior is more than sufficient for most purposes.

I highly value LessWrong and can't think of any reasons why I would want to do it harm.

Nothing I have said suggests this. Indeed, this is explicitly incompatible with my words as I have written them and it is bizarre that it has come up. Once again, to be even more clear, Wei Dai's sincerity and pro-social intent have never been questioned. Indeed, I riddled the entire preceding conversation from my first reply onward with constant disclaimers to that effect to the extent that I would have considered any more to be outright spamming.

(nods) FWIW, I'm entirely unsurprised by this. What I'm not quite sure of is whether Wei Dai shares our view of what you believe in this space. I'm left with a niggling suspicion that you and he are not using certain key terms equivalently.