I read both your response and kb's. Funny thing was, when I saw your original comment, my first thought was to suggest you make it its own thread. I was afraid a one-line response would seem flip, though, and I wasn't able to respond in detail at the time.
It is interesting to see tng's response to this question because I never interpreted the "thoughtful web" to refer to the structure of Hubski. I always thought it was about the content and perhaps a reminder to keep responses and discussion thoughtful. Indeed, even if that's not what it's meant to refer to, I think that most of the founders' ideas about this site focus on discussion and at that, quality discussion. Or at least that such discussion is one of the primary goals of this site, not simply to aggregate links in terms of the mutual community's interests.This interpretation of the motto has caused me to monitor my commenting behavior, striving to leave comments that contribute to the site, not one-liners or puns or etc. If I absolutely feel the need to make some sort of one-line joke in response to what someone else has written I try to also leave something responding to their actual point. Yes, sometimes I leave one-line replies and honestly sometimes that's all that's warranted - but most of the time I try to give more and I try to give a lot of thought to responses.
For me it's about quality and quantity. Sometimes taking a day or two to respond to a comment until I have the time. (People who DM me know that sometimes I fall off the DMs for a week or two. I just need some time to respond to stuff sometimes.) At least, that's in terms of the comments.
For links - I read stories before I decide to share them. I share them if I find them really thought-provoking or fascinating. If it's an 8-page article that I can't tear my eyes away from for at least two pages, oh heck yes I'm sharing. This comes down to personal preference though. But I guess it's how I avoid giving an "upvote" for the sake of patting someone on the back. There are some discussions I follow but I don't share. There are some threads I'm very active in but don't share. It's because although I find the topic interesting I wouldn't normally have clicked on it, or something. That's harder to explain.
For posting in #askhubski one of my mostly-held-to-guidelines is I try to ask questions I don't know the answer to. This honestly kind of limits me on "story" threads but I don't know as that's a totally bad thing. At some point those can get really out of hand. (Note, of course, I have posted story threads before. I said "mostly-held-to.") As a result I mostly post questions I've been chewing over in my head that I can't figure out. "Is lying bad?" - still not convinced. But a great discussion. Meta-hubski questions are pretty big for me too I guess. I've posted a few. Usually because I've been chewing them over in my head I've got a lot of thoughts on the topic which I think sets a good groundpoint for a thoughtful discussion. It's interesting to see everyone's different perspective on something and I really enjoy seeing how everyone thinks differently. It's a good reminder of how different we all are inside of our heads.
What makes a thing thoughtful? I think the amount of time you've put into considering it, the length of what you have to say about it, and the quality of that quantity. If you have a lot to say and it's not drivel - better yet if it's driven by passion - it's probably thoughtful.
This is a high standard of course and you can't be 100% thoughtful 100% of the time. A discussion peters out at some point. But, heh, there's my ruminations.