[Wine] Using wine for legacy support under windows?

[mr jingle]

I know it's totally unsupported and probably even a stupid question to ask considering that it's a topic that is nowhere to be discussed in the wiki, but I hope that someone with more clue could help me.

I need to deploy on several machines (laptop) running vista 64 bit an old 16 bit accounting /groupware/calendar application, which is, of course, custom, proprietary and no longer supported by the developer (which was a local developer and has closed since a while, by the way)

Despite of that, it runs decently enough on wine to use it as a temporary solution.

Considering that downgrading the vista machines to 32 bit is a "no go" and that using a virtual machine on every single laptop would be a great pain to support, is there a way to package a windows application on windows the same way that , for example, picasa is packaged to run under linux? even by using cygwin/X is an acceptable solution.

PS: Yeah, I know that after reading the wiki I should know the (negative) answer. I can only hope that some documentation regarding wine on windows is severely outdated or I'm missing something.  :P