Thoughts on how to do it:
Use dosbox? http://www.dosbox.com/news.php?show_news=1
Use a vm for old apps? Vmware and or Bochs or Qemu with an install of an older OS?
Fix the 16 bit subsystem for the issues that have existed for a long time :-) http://www.vttoth.com/wow32.htm
For the error:
Application popup: Application: SO_AAM2 : The Win 16 Subsystem has insufficent resources to continue running. Click on OK, close your applications, and restart your machine.