I’ve been following this series and it’s been extremely helpful.

I started setting up something very similar with Cowork’s productivity plug in. But I ran into trouble because it kept getting confused as to directories. It seemed to be because I was using iCloud Drive. I was doing so not only for back up reasons, but so that I could access info on my phone (via Obsidian).

I switched to Claude Chat, and it’s been working great. I upload my ClaudeMD file, daily note, and if relevant projectmd files. We chat about the priorities etc. and Claude gives me updated files with briefings for the day, week etc.

The advantage of chat seems to be that it uses session and token limits more slowly. The disadvantage seems to be that it is a slight faff to upload and download the files.

Did you run into similar issues with Cowork finding directories? How do you decide when to choose between Code, Cowork and Chat these days?