I think Out is making good informing people about the state of his work. Just estimate when minimally/maximally work will be done, and description why short/long this time. No need in asking questions, for me.
As for stupid questions, there are different things when many customers and programmer supporting product, and when you develop just for one customer. In first situation, manager should talk to customers and aggregate info to programmer, in second - it depends on agreements between customer and your company. Customer can ask to be able to control work, and can just want result and dont bother tracking.