My first inclination is that putting out a larger volume of potentially correct work and letting it go through trial-by-fire and be discussed is superior to waiting until an argument is fully bulletproofed, caveat'ed, and so on.

Definitely depends on what your goals are. If you're interested in getting feedback for your ideas while stimulating discussion then doing what you did except with more of a "but that's my take on it and I'm not completely satisfied with it yet, what does Less Wrong think?" approach will get more useful feedback. Posting things somewhat-haphazardly will get you more feedback on background/meta stuff, like the things I've focused on in my comment replies, which can be useful but can also backfire in non-obvious ways. Your reputation might get hurt to some extent, which will cause you to get less upvotes and attention in the future when you want people to really pay attention to your well-thought-out ideas. I think this downside is very easy to underestimate. I tentatively think (though I haven't done a quantitative analysis and there are many other possible explanations) that I used to get a lot more karma per comment before I started posting about things that had way too much inferential distance, or that pattern-matched to things people believe for silly reasons. That was about 4 months ago.