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Re:Wine 3.0 Released by dfox on Thursday January 18, 2018 @03:23PM (#16181009)
This is one issue, another issue is that the method used to implement 16-bit compatibility in 32b windows involves virtual 8086 mode and running instance of DOS inside of that even for native 16b windows applications.

In all, I assume that it was droped mostly because it involved too much work for somewhat questionable benefit.

Re:Wine 3.0 Released by JdeBP on Friday January 19, 2018 @01:11PM (#16188354)
That won't have been the issue. Win16 programs never ran in v8086 mode, even on DOS-Windows 3.1. They ran in the normal 16-bit protected mode.