I did tech support when the 99->00 switch happened, got paid 3x overtime. I got one call, and it was actually legitimate, but was a third party piece of software so after that we left and went to a party :)

I doubt this will be a real problem in 2038, then again the prevalence of computing devices is much larger now and will continue to grow by 2038, but so will technical aptitude, so hopefully they'll cancel out and this will still not be a problem.