I guess the problem with the 2038 hard limit is that there's genuinely a lot of very good 32-bit x86 hardware that will stay working into the far future. I know people that swear by Panasonic Toughbooks and use them daily, and that hardware isn't going to die any time soon - same with industrial PCs, PC Engines, and Soekris boards. I'm against electronic waste, if it works and is efficient it should stay working.
The way NetBSD chose to do 64-bit time_t is probably weird. OpenBSD later did it by breaking ABI, but NetBSD did it by versioning system calls. The old 32-bit time_t system calls still exist and will be used if you run a binary that was built before the switch, on the whole making the switch painless.