Have you seen what's going on on google code? https://code.google.com/p/thematic/
That's where all development happens, and the recent weeks have shown quite some movement forward.
The upcoming version of thematic includes a revamp to make it adhere to the latest theme review requirements, an extendable options page using the Settings API, general code cleanup and other things. It is getting close to being submitted to the wordpress repo for review and subsequent release. Testers are always needed, so download the latest version if you can and help to squash out any bugs. That means, report any you find so that the developers can squash them. :)
Regarding HTML5, that is a discussion for a future version (since the upcoming is so close to ready I don't think HTML5 will get into that one). What to do and how to handle it. Thematic cannot just switch to HTML5 straight away since that would break existing sites. So the question is how to handle backwards compatibility, make a clean fork and create a separate HTML5 version, use some kind of switch with double code in the framework, or some other brilliant idea. Your input is welcome.
I started working on a plugin that will switch the markup to HTML5 elements, but it is so far just a start. Meaning, it works, but lacks polish and is somewhat untested. Feel free to comment and report bugs/request features there as well. https://github.com/middlesister/thematic-html5
Regarding hiring a developer, well that requires knowing what that developer would do! Since things are moving forward at the moment I don't know if that would be necessary. If you would like to add some page templates, add feature requests for what you miss and see if other people also need them. If and when we know specific features that we want and nobody has the time or ability to make it happen, well then maybe the topic can be raised again. In the meantime: Welcome to Thematic and join in the discussion of the future!