If I remember correctly from the DOS times, the limit for com files was 64KB. I haven't tried to compile one for ages, is this any different on Windows NT+ (I would try but I dont have a single windows machine at home)?
The Wikipedia page for .com suggests that 64 bit Windows NT+ systems can't run the original style .com files anymore due to lacking the MS-DOS emulation subsystem, so the point may be moot.
Totally cheating would be to integrate the DOS application functionally into the Windows DOS stub. Instead of printing "This application requires Microsoft Windows" it could even use overlays to circumvent the 64kB com restriction.