Start a context when a separate topic appears with its own goal and agreements. A form fix, a shop migration and an experiment can each have their own conversation.
There is no single number that fits every project. The names and short summaries should show what is done, what is waiting for a decision and where to resume.
Parallel sessions are limited by the machine’s resources and the limits of your AI accounts. In the AI Sessions view you can check active processes across all projects and end the ones you no longer need.