Thanks for your story. I've heard that from so many people. That Octopress opened doors for them and exposed them to new interests. It's pretty much the best thing I could ask to hear. I love that I was able to be a part of that spark for people. So, thanks for sharing!
For what it's worth, I'm also a huge fan of Middleman. It's a great project and I use it for some things too. For a while, when Jekyll was in a dry spell, I considered building Octopress tools for Middleman as well, but in the end I prefer the simplicity of Jekyll.
Middleman is great, but it's too much like the view layer of Rails. To me, Jekyll feels more like the native web.
There are people who use Jekyll for multilingual blogging without any special plugin. Since I don't, I'm not sure I can give you advice on the best technique. A bit of Googling and you'll be set.
If you find a workflow that works for you, post an issue on GitHub and maybe I can help automate parts of it. If it's just about adding YAML data, the new post templates feature of Octopress should take care of you there.
Not sure why you'd say "bad timing". Moving to Vanilla Jekyll is the right decision. You'll be able to use any and all of the new plugins. There's no distinction anymore.
I look at GitHub issues and I'm just afraid to mess with things. Even if I fix stuff, there's a high likelihood that it will break something else or be hard to update to. I too cannot wait to release this.
There have been people over the years who've been eager to build a GUI for Octopress. Without a good CLI it would be a huge pain. Many of the things I've been working on, should make it easier for that to happen.
Octopress has slowed down due to my need for help with a few things. I've tried working with a few folks, but it hasn't worked out. Now I'm getting the help I need and things are cranking up again. Believing that Jekyll has a future is a great motivator too.
For what it's worth, I'm also a huge fan of Middleman. It's a great project and I use it for some things too. For a while, when Jekyll was in a dry spell, I considered building Octopress tools for Middleman as well, but in the end I prefer the simplicity of Jekyll.
Middleman is great, but it's too much like the view layer of Rails. To me, Jekyll feels more like the native web.