Working at a startup with a small (~4-6) person engineering team usually means those few people are the most in tune with the software. This then usually leads to an onslaught of people who should know better asking devs stupid questions about the software or relying on the devs to do their jobs for them.

Have you encountered these types of situations before? How were they resolved?

I did in a way. Not a startup but a new team where all members were juniors except the team leader. Somehow we managed to deliver the first product and then another. And then another one. In the meantime the team was decimated (if we consider 10 as a binary number, half of the team left over a period of 6 months).
After that more young people joined. The team leader was stretched thin over the several projects the team was now responsible for however so it was our responsibility (the survivors) to help the newbies.
Answer their questions, make them write the answers down and then supervise them doing it (do not intervene if not strictly necessary) using their notes.
Few things as are annoying as relying on notes. You may have to answer the same question twice but very rarely they will ask the same question three times.

P.s. if they reach repetition number five several times scold them. If they continue fire them.

small person team? like midgets? and everyone is midget who has height from 4 feet to 6 feet?