With current changes in my life, it looks like I'll be updating here for frequently.
The good news is that I've finally gotten around to reviving Timothy into a proper product.
The old 0.1.X version was focused on a single task with the highlight being the chatbot interface.The new version (0.2.0) will launch without any machine learning aspects at all. Instead the focus will be on Timothy remembering and reminding you of all the things you wouldn't normally put on your calendar but otherwise clutter up your mind - like when to water which plants or vacuum upstairs or take out the trash.
After that the product roadmap is to add on the chatbot interface, first in the web and then in a mobile app.
This of course means I'll need to find out someway to create mobile apps.
Assuming I manage all of that, then I'll start working on things like having Timothy optimize task distribution and suggesting new tasks based on prior history and comparisons with similar users.
That should keep me adequately busy.