Aside from filling in the timesheet (which I assume could be done from a CSV import - I appreciate this is another step), I have almost the same setup as you, without AI. I have bugwarrior pulling JIRA tickets and github PRs into taskwarrior. I have an integration from task warrior into time warrior and from there another hook back into JIRA to get titles and summarise.

All of that is done with two API keys and no AI. A local agent could easily put it together for you.

Now sure, I had to put this together and I lose the AI summary you have plus the auto filling, but what I'm trying to say is that I have 80% of this without any AI.

I also have a script parsing git from my emails and a little tui that translates them into git diff and a key binding to pull the PR but I find it a little cumbersome and don't really use it, and trying to parse todo from maildir is also a little useless so I accept that AI would be better there.

I also accept that your example is just one prompt of a dozen and I have to plan the solution for every one of your prompts, but I also don't find prompting to be terribly useful for occasions where I don't think the solution through- because it probably means I don't know what I want or don't really need it.

What I do find it really useful for is digging through Kubernetes and asking how two services are connected. Claude is better than local for that but there's nothing inherently non-local about that usage.