Dialogs are still a serious problem with Word and other applications. If you are able to generate, reliably and accurately, a “transportable” format that you know your version will accept, then that is definitely a good alternative. It will probably be best to let the Microsoft application itself generate the document that can then be used as a programmatic basis for what comes next, e.g. by turning it into a Template or something like that. But it can still turn out to be a crap-shoot.
If you do use a Perl module to generate the base document, I definitely would shoot for one of these transportable formats, versus trying to emulate Microsoft’s file-madnesses ... and in any case I would be sure to use the most-current and most-recently-updated CPAN module that you can possibly lay your hands on, whatever one that turns out to be. If it is “a few years old,” even, there could be problems. Test the holy-hell out of whatever you do finally come up with, and then pray that Redmond will smile.