I know nothing about the topic. I'll only point out that https://bugs.winehq.org/show_bug.cgi?id=36664 says ".. the reality in the past the 16 bit code was not a issue because the [Linux] kernel always supported it." and "...3.15 after 16 bit support by [Linux] kernel is optional on 64 bit systems."

That links to lmkl posts like https://lkml.org/lkml/2014/4/14/207

>> Afaik 64-bit windows doesn't support 16-bit binaries, so I just assumed Wine wouldn't do it either on x86-64. Not for any real technical reasons, though.

> Yes, there is still a significant number of users, and we still regularly get bug reports about specific 16-bit apps. It would be really nice if we could continue to support them on x86-64, particularly since Microsoft doesn't ;-)