Hm, Y2K issues were the result of conscious design trade-offs, not bugs. (Nobody ever looked back and said: oops, we accidentally left the century off of our dates.)
I do wonder what 2038 is going to bring since it goes well beyond the IT department. I get the feeling the bill is going to be massive. I'm just glad we finally were able to replace the Windows 95 box running the boilers.
Corollary: The most expensive bugs to fix are the oldest bugs.