IANAL, but he should have revised his damages for the second case to account for his expenses, including time. He probably could have won closer to $6000 without a problem.

The author comes off as deeply uninformed about how legal proceedings in the U.S. work, for example talking about how he had to refute arguments in court and such, which is just not how things work at all at that level. Some basic Googleing would have taught him all he needed to know about defending himself in small claims court without stress.