I got Drupal 6.6 installed, and then someone suggested Acquia Drupal (more bundled modules, and it integrates with Acquia's brand-new network services and support). So I installed that. Not too bad, but definitely more involved than my original hosted one-click WordPress install.

It's doing SSL and I have Apache mapping a couple vhosts to the main Drupal installation per http://drupal.org/getting-started/6/install/multi-site, but I don't want to deal with a mix of shared and unique MySQL tables across sites.

Drupal's blogging is pretty basic, and it's not immediately obvious how to promote vhosts to top-level virtual hosts (probably mod_rewrite, which seems pretty central to Drupal). I'm not sure how easy it would be to hide the non-blog parts of Drupal I'm not interested in, and there's no WYSIWYG built-in. I like to write raw Markdown or HTML, but one of my goals is to make it easy to host blogs for friends & family, who generally want WYSIWIG. I found YUI Editor, but Yahoo is pretty confused about it today, and the instructions are lacking.

So for now, it looks like I'm going to set up 3 more personal WP blogs, and hope that in a year or two either WP-MU gets better SSL support, or Movable Type becomes more attractive. I guess I should try DotClear first, as they tell me it handle logins for multiple blogs through a shared site.