On the other hand, I'd argue companies using 16-bit applications would be unwilling to upgrade to a 64-bit installation anyway. Microsoft decided it was better to push software developers to upgrade to Win32, given that 32-bit Windows already existed since 95.
Sure, but the 16-bit program that was still being used the most had to be setup.exe or install.exe. For many years it was common to distribute all software packages with a 16-bit installer because it's (slightly) smaller and it's never doing anything that would require 32-bit processing.
So, now, it's not unusual to find software from as late as 2005 that is actually 32-bit software, but it's in a 16-bit installer.
Indeed, it might be the only 16-bit application I've wanted to run other than Castle of the Winds and Scorched Earth.