It matters only if you hit your plan usage limits. If you don't then who cares. My fresh sessions are minimal and I hit my weekly $100 max plan lately. No one else can tell you wether 20/30/50k is bad. If your setup needs that much to run well than it's good and if you hit your limits it's time to upgrade your plan Obviously the smaller and concise the context the better because the bigger it gets the worse the llm will perform

@Ryan Doser oh no worries, that's just a standard feeling that entrepreneurship comes with 🤣

@Nesil Ozer yup, more insights and then you over think again instead of take action 🤣

@Catherine Eadie probably. It's cheap ,you can access your data from anywhere and their servers most likely have better security. Buut I still like to have a local copy

@Catherine Eadie wow 😳 that's a huge price increase. I think they're here to stay, with all the demand for data centers now

Welcome to the group @Tim Naylor !

I'm not sure how Cowork differs from Claude code in this regard. But I would create a strict project system for Claude: CLAUDE.md = rules for Claude PROJECT_STATE.md = where the project stands right now TASKS.md = what to build next CLAUDE.md tells Claude how to behave in the project, what rules to follow, what not to touch, how to test, and how to report back. PROJECT_STATE.md tells Claude where the app build currently is, what has already been built, what is broken, what decisions were made, and where things stand. TASKS.md lists the next work orders/tasks Claude should complete. In your CLAUDE.md you can say something like: "Before coding, read PROJECT_STATE.md, TASKS.md, and relevant files. Do not start new features unless the current task is complete. After each task, run tests, update PROJECT_STATE.md, and summarize changed files." Also use Git so you always have save points to go back to if something breaks or goes off track. Plan out your work orders and create a WO to do list. Make each build small and specific instead of trying to everything at once. This will be easier for him to stay on track. I also keep a hard copy of the work order list in a doc so I could quickly check that he's following the work order correctly (example of my work order description attached) This helps!