Don't be afraid to do the next least janky thing. Run with it. It's like David Allen with GTD:
If you can't do it with paper, you don't understand your process enough yet.
A manual process that is well understood can be well automated, an undefined process will struggle as automating something while also defining something always ends being a huge long project. If you can mentally model how to do it in trello, then do it, and come back to the automation step once you see it working (they have an API, you can get there).
