Comments I'm proud of are frequently ignored, and comments that I think are cheap tricks frequently get upvoted.

This. Very much this. Not a lot of my stuff gets upvoted. Yesterday I think, I had an existential crisis about it "oh my god, do I suck?". Yes that's stupid, but I often find it deeply disturbing that I am not a demigod.

LW is better than reddit, but yeah.

Another observation is that the downvoters seem to come out first. Posts (articles in discussion, specifically) that end up highly voted usually start out hovering around zero or going negative before rising. This post for example.

EDIT: Actually, I'd really like to see some graphs and stats on this from the LW database. Another thing to get more useful data is to allow people to cast a vote for which of their own comments they are most proud of, and see if this vote correlates with community vote.