Another fan of Fusion Pro Desktop here. This is exactly what you need. We have sold both PrintShop Mail and Fusion Pro Desktop for this very application (numbering) and other VDP applications. Fusion Pro Desktop easily beats PrintShop Mail from both a price and performance viewpoint. You could also try Printer's Bench for a good entry level package

You can use Microsoft Word to create complex documents. Books and other large documents occasionally require different page number formats in different sections of one document. For example, you can number the index pages with Roman numerals (for example, "i.", "ii.", "iii.") and the main document with Arabic numerals (for example, "1", "2", "3"). This article describes how to set up different page numbering formats.
Notice that the Font option (when you applied italics) changes only the number, not the heading text. To update the heading text, modify the heading style as you normally would. Word assumes you want all Heading 1 and Heading 2 styles included in the new numbering scheme. If you want to omit a heading level from the scheme, don't use a built-in heading style to format those headings.
You can control whether your next paragraph number continues the current sequence or starts again at 1 within that same right-click menu. If one of your numbers gets out of sequence, simply right-click and choose Continue Numbering. If you want to force the number back to the beginning (say, you’re switching from interrogatories to requests for production), choose Set Numbering Value (which will also give you the option of continuing the previous list).

Changing the numbering display affects how pages are indicated in the InDesign document, as in the Pages panel and in the page box at the bottom of a document window. The numbering display also affects how you specify page ranges when printing and exporting the document. However, the numbering display does not change the appearance of page numbers on document pages. numbering in indesign