Yes, many DOS console apps don't work under plain Wine because DOS emulation does not create console for the applications. Some applications actually make Wine crash because the application gets illegal coordinates when GetConsoleScreenBufferInfo fails.
The correct place for console allocation would likely be VGA_SetAlphaMode; call to normal Windows AllocConsole() function should be enough, no server calls are needed. Additionally, if DOS console application tries to call a routine that requires console, VGA_SetAlphaMode should be called in order to initialize console (see VGA_SetCursorPos).
I have been thinking doing this myself, but I have always ended up being uncertain about how this change is going to affect piping input and output of DOS programs that use only stream IO and not console IO. Anyway, I don't have time for this stuff so I would appreciate if you could work on this.