Is it okay to ask Claude very basic or 'dumb' questions, and how does that help improve workflows?

There's no such thing as a dumb question to ask Claude. Asking basic questions is part of how you learn and improve your own workflow. If something feels hard or takes too long, ask Claude how it could be done better next time — it will recommend workflow improvements. That's the point at which it makes sense to start creating skills for repeated tasks, running them, reviewing the output, and iterating to improve the skill over time.