I just realized I forgot to mention up here a cute little hack I wrote a while ago called rst2wp. It's basically a Wordpress client with a few neat features, customized to my workflow:

1. Reads source in ReStructuredText, which is the most coherent plaintext-formatting language out there.
2. Lets you specify tags, not just categories (unlike most WP clients I've found).

3. Searches for image tags in each post, downloads them, and then uploads them to your server (so you don't hotlink images).

It's already successfully running my travelogue.

The docstring in the source is the only documentation so far. Any questions, email me.