Tonight I finally started down the road of removing cruft from my URLs like Mark. Unfortunately, it looks my web host doesn't let me set redirects in my .htaccess file at the moment (that or I'm too tired to figure out what I'm doing wrong).
I did at least get one part working. The main complaint I had about my previous URL design is that the paths that appear in my logs are not especially readable. I don't recognize my posts by their numerical id. Sure I could write some code to replace the id with the title. I could also spend that time skiing. So I've added the thing Mark called a 'slug' instead of the numerical id. This shouldn't effect the older posts (except the last two which I used to test the concept).
I would still like to get rid of the .html part, and give meaningful names to some of my older posts. The trick will be preserving the old links with some permanent (301) redirects. Maybe I'll get to that by next year. ;-)