I write you from the future! I, as predicted, made the switch over between the wordpress powered version of tychoish.com and the jekyll powered version of my site. I'm quite pleased with this development. Basically it works by taking a repository of posts with all the content from my site and then compiles a website of static pages whenever I trigger an update. Though it hasn't worked flawlessly, I'm pretty pleased with how this has worked out, and as I clean things up and get to using the system a bit more I'll write up a post regarding jekyll, but I want to get used to it some more.
The biggest change is that I'm now calling the short form posts, "notes" and the long form posts, "essays" (as usual) and I've changed the landing page a bit. In all I think it's an improvement. I'm not done tinkering around here: I hope this system will make it easier to develop and "curation" lists of related content. If I learned nothing else from this project, it's that I have a lot hanging around in the archives, and the chronological list of content isn't a particularly good presentation of this. So new ways of visualizing the content are in store.
Also, if you're inclined, you can get a copy of the repository that powers this site over on github. I'll set up local hosting/cloning of the git repository, in a bit.
Anyway, Onward and Upward indeed!